CTLP / Cantaloupe, Inc. - SEC-Einreichungen, Jahresbericht, Proxy Statement

Cantaloupe, Inc.
US ˙ NasdaqGS ˙ US1381031061
DIESES SYMBOL IST NICHT MEHR AKTIV

Basisstatistiken
LEI 529900O54DBQQVWO9Q85
CIK 896429
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Cantaloupe, Inc.
SEC Filings (Chronological Order)
Auf dieser Seite finden Sie eine vollständige, chronologische Liste der SEC-Einreichungen, mit Ausnahme der Eigentumseinreichungen, die wir an anderer Stelle bereitstellen.
May 18, 2026 15-12G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 15 CERTIFICATION AND NOTICE OF TERMINATION OF REGISTRATION UNDER SECTION 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR SUSPENSION OF DUTY TO FILE REPORTS UNDER SECTIONS 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 15 CERTIFICATION AND NOTICE OF TERMINATION OF REGISTRATION UNDER SECTION 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR SUSPENSION OF DUTY TO FILE REPORTS UNDER SECTIONS 13 AND 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number 001-33365 Cantaloupe, Inc. (Exact name of registrant as specified in its char

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May 8, 2026 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): May 8, 2026 Cantaloupe, Inc. (Exa

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): May 8, 2026 Cantaloupe, Inc. (Exact name of Registrant as Specified in its Charter) Pennsylvania 001-33365 23-2679963 (State or other Jurisdiction of Incorporation) (Commission File N

May 8, 2026 S-8 POS

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May 6, 2026 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2026 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact name o

May 1, 2026 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): May 1, 2026 Cantaloupe, Inc. (Exa

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): May 1, 2026 Cantaloupe, Inc. (Exact name of Registrant as Specified in its Charter) Pennsylvania 001-33365 23-2679963 (State or other Jurisdiction of Incorporation) (Commission File N

May 1, 2026 EX-99.1

CANTALOUPE, INC. NOTICE OF REDEMPTION SERIES A CONVERTIBLE PREFERRED STOCK CUSIP NO. 138103205

Exhibit 99.1 Execution Version CANTALOUPE, INC. NOTICE OF REDEMPTION SERIES A CONVERTIBLE PREFERRED STOCK CUSIP NO. 138103205 Holders of Cantaloupe, Inc.’s Series A Convertible Preferred Stock: Reference is hereby made to (i) the Amended and Restated Articles of Incorporation, as Amended Through April 15, 2021 (the “Articles”) of Cantaloupe, Inc., a Pennsylvania corporation (the “Company”), and (i

February 6, 2026 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended December 31, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact nam

November 21, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 19, 2025 Date of Report (date of earliest event reported) Cantaloupe, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 19, 2025 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organizatio

November 6, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact na

October 10, 2025 ARS

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UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended June 30, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact name of registra

October 10, 2025 DEF 14A

SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 ☑ Filed by the Registrant ☐ Filed by a party other than the Registrant CHECK THE APPROPRIATE BOX: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☑ Definitive Proxy State

September 24, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): September 24, 2025 Cantaloupe, In

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): September 24, 2025 Cantaloupe, Inc. (Exact name of Registrant as Specified in its Charter) Pennsylvania 001-33365 23-2679963 (State or other Jurisdiction of Incorporation) (Commission

September 18, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): September 18, 2025 (September 17,

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): September 18, 2025 (September 17, 2025) Cantaloupe, Inc. (Exact name of Registrant as Specified in its Charter) Pennsylvania 001-33365 23-2679963 (State or other Jurisdiction of Incor

September 8, 2025 EX-4.1

DESCRIPTION OF SECURITIES REGISTERED PURSUANT TO SECTION 12 OF SECURITIES EXCHANGE ACT OF 1934

Exhibit 4.1 DESCRIPTION OF SECURITIES REGISTERED PURSUANT TO SECTION 12 OF SECURITIES EXCHANGE ACT OF 1934 As of June 30, 2023, Cantaloupe, Inc. has two classes of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”): (1) our Common Stock; (2) our Preferred Stock. Authorized Capital Shares Our authorized capital shares consist of 640,000,00

September 8, 2025 EX-19.1

CANTALOUPE, INC. INSIDER TRADING COMPLIANCE POLICY (As adopted on September 5, 2024)

Exhibit 19.1 CANTALOUPE, INC. INSIDER TRADING COMPLIANCE POLICY (As adopted on September 5, 2024) This Insider Trading Compliance Policy (the “Policy”) concerns the handling of material, non-public information relating to Cantaloupe, Inc. (“Cantaloupe”, the “Company”, “our” or “we”) or other companies with which we deal and with the buying and selling of stock and other securities of Cantaloupe an

September 8, 2025 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended June 30, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact name of registra

September 8, 2025 EX-97.1

Cantaloupe, Inc. Amended and Restated Incentive Compensation Clawback Policy (Effective as of October 2, 2023)

Exhibit 97.1 Cantaloupe, Inc. Amended and Restated Incentive Compensation Clawback Policy (Effective as of October 2, 2023) The Board of Directors (the “Board”) of Cantaloupe, Inc. (the “Company”) has determined that, in addition to the Company’s Dodd-Frank Wall Street Reform and Consumer Protection Act of 2010 clawback policy applicable to executive officers (the “Dodd-Frank Clawback Policy”), it

September 8, 2025 EX-10.94

CANTALOUPE, INC. 2018 EQUITY INCENTIVE PLAN NOTICE OF RESTRICTED STOCK UNIT GRANT AND RESTRICTED STOCK UNIT AWARD AGREEMENT

Exhibit 10.9.4 CANTALOUPE, INC. 2018 EQUITY INCENTIVE PLAN NOTICE OF RESTRICTED STOCK UNIT GRANT AND RESTRICTED STOCK UNIT AWARD AGREEMENT Cantaloupe, Inc., a Pennsylvania corporation, f/k/a USA Technologies, Inc. (the “Company”), pursuant to its 2018 Equity Incentive Plan (as amended from time to time, the “Plan”) hereby grants to the holder listed below (the “Participant”) an award of restricted

September 8, 2025 EX-10.93

CANTALOUPE, INC. 2018 EQUITY INCENTIVE PLAN NOTICE OF NON-QUALIFIED STOCK OPTION GRANT AND NON-QUALIFIED STOCK OPTION AGREEMENT

Exhibit 10.9.3 CANTALOUPE, INC. 2018 EQUITY INCENTIVE PLAN NOTICE OF NON-QUALIFIED STOCK OPTION GRANT AND NON-QUALIFIED STOCK OPTION AGREEMENT Cantaloupe, Inc., a Pennsylvania corporation, f/k/a USA Technologies, Inc. (the “Company”), pursuant to its 2018 Equity Incentive Plan (as amended from time to time, the “Plan”) hereby grants to the holder listed below (the “Participant”) a non-qualified st

September 8, 2025 EX-21.1

SUBSIDIARIES OF THE REGISTRANT

Exhibit 21.1 SUBSIDIARIES OF THE REGISTRANT Subsidiary State or Province of Incorporation Country of Incorporation Cantaloupe Solutions Canada, Inc. British Columbia Canada Cantaloupe International, Inc. Delaware United States Cantaloupe Systems, Inc. Delaware United States Stitch Networks Corporation Delaware United States USAT Capital Corp, LLC. Pennsylvania United States Three Square Market, In

September 4, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): September 4, 2025 Cantaloupe, Inc

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): September 4, 2025 Cantaloupe, Inc. (Exact name of Registrant as Specified in its Charter) Pennsylvania 001-33365 23-2679963 (State or other Jurisdiction of Incorporation) (Commission

August 22, 2025 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Definitive Proxy State

July 24, 2025 DEFM14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A   Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant  ☐ Check the appropriate box:  ☐ Preliminary Proxy Statement  ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒

July 11, 2025 PREM14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A   Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant  ☐ Check the appropriate box: ☒ Preliminary Proxy Statement  ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))  ☐

July 11, 2025 EX-FILING FEES

CALCULATION OF FILING FEE TABLES Schedule 14A (Form Type) Cantaloupe, Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Transaction Valuation

Exhibit 107 CALCULATION OF FILING FEE TABLES Schedule 14A (Form Type) Cantaloupe, Inc.

June 16, 2025 EX-2.1

AGREEMENT AND PLAN OF MERGER dated as of June 15, 2025 by and among CANTALOUPE, INC., 365 Retail Markets, LLC, CATALYST HOLDCO I, INC., CATALYST HOLDCO II, INC. CATALYST MERGERSUB INC. Table of Contents

Exhibit 2.1 EXECUTION VERSION AGREEMENT AND PLAN OF MERGER dated as of June 15, 2025 by and among CANTALOUPE, INC., 365 Retail Markets, LLC, CATALYST HOLDCO I, INC., CATALYST HOLDCO II, INC. and CATALYST MERGERSUB INC. Table of Contents Page Article 1 Definitions 1 Section 1.01. Definitions 1 Section 1.02. Other Definitional and Interpretative Provisions 13 Article 2 The Merger 14 Section 2.01. Th

June 16, 2025 EX-99.1

Cantaloupe, Inc. Enters into Definitive Agreement to Be Acquired by 365 Retail Markets Cantaloupe shareholders to receive $11.20 per share in cash, a 34% premium to unaffected stock price Transaction to accelerate growth in unattended retail and enha

Exhibit 99.1 Cantaloupe, Inc. Enters into Definitive Agreement to Be Acquired by 365 Retail Markets Cantaloupe shareholders to receive $11.20 per share in cash, a 34% premium to unaffected stock price Transaction to accelerate growth in unattended retail and enhance product offering for customers in fast-growing markets and verticals MALVERN, Pa. and TROY, Mich. – June 16, 2025 – Cantaloupe, Inc.

June 16, 2025 EX-99.1

Cantaloupe, Inc. Enters into Definitive Agreement to Be Acquired by 365 Retail Markets Cantaloupe shareholders to receive $11.20 per share in cash, a 34% premium to unaffected stock price Transaction to accelerate growth in unattended retail and enha

Exhibit 99.1 Cantaloupe, Inc. Enters into Definitive Agreement to Be Acquired by 365 Retail Markets Cantaloupe shareholders to receive $11.20 per share in cash, a 34% premium to unaffected stock price Transaction to accelerate growth in unattended retail and enhance product offering for customers in fast-growing markets and verticals MALVERN, Pa. and TROY, Mich. – June 16, 2025 – Cantaloupe, Inc.

June 16, 2025 EX-10.1

VOTING AND SUPPORT AGREEMENT

Exhibit 10.1 VOTING AND SUPPORT AGREEMENT This Voting and Support Agreement (this “Agreement”) is entered into as of June 15, 2025, by and between 365 Retail Markets, LLC a Delaware limited liability company (“Parent”), and [●] (“Shareholder”). Capitalized terms used but not otherwise defined in this Agreement have the meanings assigned to such terms in the Merger Agreement (as defined below). W I

June 16, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): June 16, 2025 (June 15, 2025) Can

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): June 16, 2025 (June 15, 2025) Cantaloupe, Inc. (Exact name of Registrant as Specified in its Charter) Pennsylvania 001-33365 23-2679963 (State or other Jurisdiction of Incorporation)

June 16, 2025 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): June 16, 2025 (June 15, 2025) Can

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): June 16, 2025 (June 15, 2025) Cantaloupe, Inc. (Exact name of Registrant as Specified in its Charter) Pennsylvania 001-33365 23-2679963 (State or other Jurisdiction of Incorporation)

June 16, 2025 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Definitive Proxy State

June 16, 2025 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨ Definitive Proxy State

June 16, 2025 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨ Definitive Proxy State

June 16, 2025 EX-10.1

VOTING AND SUPPORT AGREEMENT

Exhibit 10.1 VOTING AND SUPPORT AGREEMENT This Voting and Support Agreement (this “Agreement”) is entered into as of June 15, 2025, by and between 365 Retail Markets, LLC a Delaware limited liability company (“Parent”), and [●] (“Shareholder”). Capitalized terms used but not otherwise defined in this Agreement have the meanings assigned to such terms in the Merger Agreement (as defined below). W I

June 16, 2025 EX-2.1

AGREEMENT AND PLAN OF MERGER dated as of June 15, 2025 by and among CANTALOUPE, INC., 365 Retail Markets, LLC, CATALYST HOLDCO I, INC., CATALYST HOLDCO II, INC. CATALYST MERGERSUB INC. Table of Contents

Exhibit 2.1 EXECUTION VERSION AGREEMENT AND PLAN OF MERGER dated as of June 15, 2025 by and among CANTALOUPE, INC., 365 Retail Markets, LLC, CATALYST HOLDCO I, INC., CATALYST HOLDCO II, INC. and CATALYST MERGERSUB INC. Table of Contents Page Article 1 Definitions 1 Section 1.01. Definitions 1 Section 1.02. Other Definitional and Interpretative Provisions 13 Article 2 The Merger 14 Section 2.01. Th

June 16, 2025 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨ Definitive Proxy State

May 8, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact name o

May 8, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 8, 2025 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 8, 2025 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization) (Co

May 8, 2025 EX-99.1

Cantaloupe, Inc. Reports Third Quarter Fiscal Year 2025 Financial Results Third Quarter 2025 Revenue increased 11.1% Year-Over-Year, to $75.4 million, driven by 10.1% YoY growth in Subscription and Transaction revenue growth Third Quarter 2025 U.S. G

Exhibit 99.1 Cantaloupe, Inc. Reports Third Quarter Fiscal Year 2025 Financial Results Third Quarter 2025 Revenue increased 11.1% Year-Over-Year, to $75.4 million, driven by 10.1% YoY growth in Subscription and Transaction revenue growth Third Quarter 2025 U.S. GAAP Net Income Applicable to Common Shares of $48.9 million and Adjusted EBITDA[1] of $13.9 million MALVERN, Pa. - May 8, 2025 - Cantalou

February 6, 2025 EX-99.1

Cantaloupe, Inc. Reports Second Quarter Fiscal Year 2025 Financial Results Second Quarter 2025 Revenue increased 12.8% Year-Over-Year, to $73.7 million, driven by 16% YoY growth in Subscription and Transaction revenue growth Second Quarter 2025 U.S.

Exhibit 99.1 Cantaloupe, Inc. Reports Second Quarter Fiscal Year 2025 Financial Results Second Quarter 2025 Revenue increased 12.8% Year-Over-Year, to $73.7 million, driven by 16% YoY growth in Subscription and Transaction revenue growth Second Quarter 2025 U.S. GAAP Net Income Applicable to Common Shares of $5.0 million and Adjusted EBITDA[1] of $10.7 million Reiterates Fiscal Year 2025 Guidance

February 6, 2025 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 6, 2025 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization

February 6, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended December 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact nam

February 5, 2025 EX-99.2

CTLP / Cantaloupe, Inc. / Oakland Hills BV - EX-99.2

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February 5, 2025 EX-10.1

Second Amended and Restated Credit Agreement, by and among the Company, certain of its subsidiaries, and

EXECUTION VERSION #513650874v21 SECOND AMENDED AND RESTATED CREDIT AGREEMENT dated as of January 31, 2025, among CANTALOUPE, INC.

February 5, 2025 EX-99.1

CTLP / Cantaloupe, Inc. / Oakland Hills BV - EX-99.1

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February 5, 2025 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 January 31, 2025 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization

November 25, 2024 8-K

Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 20, 2024 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organizatio

November 14, 2024 SC 13G/A

CTLP / Cantaloupe, Inc. / Antara Capital LP Passive Investment

SC 13G/A 1 formsc13ga-cantaloupe.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G (Amendment No. 1) (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1(b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2(b) Cantaloupe, Inc. (Name of Issuer) Common Stock, no par value (Title of Class of Securities) 138103106 (

November 7, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact na

November 7, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 7, 2024 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization

November 7, 2024 EX-99.1

Cantaloupe, Inc. Reports First Quarter Fiscal Year 2025 Financial Results

Exhibit 99.1 Cantaloupe, Inc. Reports First Quarter Fiscal Year 2025 Financial Results First Quarter 2025 Revenue increased 13.0% Year-Over-Year, to $70.8 Million, driven by 15.7% YoY growth in Subscription and Transaction revenue growth First Quarter 2025 U.S. GAAP Net Income Applicable to Common Shares of $3.3 million and Adjusted EBITDA[1] of $9.0 million Reiterates Fiscal Year 2025 Guidance MA

October 4, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 ☑ Filed by the Registrant ☐ Filed by a party other than the Registrant CHECK THE APPROPRIATE BOX: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Definitive Proxy State

October 4, 2024 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 ☑ Filed by the Registrant ☐ Filed by a party other than the Registrant CHECK THE APPROPRIATE BOX: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☑ Definitive Proxy State

October 4, 2024 ARS

ARS

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended June 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact name of registra

September 10, 2024 EX-10.9 3

Form of Nonqualified Stock Option Award Agreement under the Cantaloupe, Inc. (f/k/a USA Technologies, Inc.) 2018 Equity Incentive Plan.

Exhibit 10.9.3 CANTALOUPE, INC. 2018 EQUITY INCENTIVE PLAN NOTICE OF NON-QUALIFIED STOCK OPTION GRANT AND NON-QUALIFIED STOCK OPTION AGREEMENT Cantaloupe, Inc., a Pennsylvania corporation, f/k/a USA Technologies, Inc. (the “Company”), pursuant to its 2018 Equity Incentive Plan (as amended from time to time, the “Plan”) hereby grants to the holder listed below (the “Participant”) a non-qualified st

September 10, 2024 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended June 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact name of registra

September 10, 2024 EX-97.1

Clawback Policy

Exhibit 97.1 Cantaloupe, Inc. Amended and Restated Incentive Compensation Clawback Policy (Effective as of October 2, 2023) The Board of Directors (the “Board”) of Cantaloupe, Inc. (the “Company”) has determined that, in addition to the Company’s Dodd-Frank Wall Street Reform and Consumer Protection Act of 2010 clawback policy applicable to executive officers (the “Dodd-Frank Clawback Policy”), it

September 10, 2024 EX-10.9 4

Form of Restricted Stock Unit Award Agreement under the Cantaloupe, Inc. (f/k/a USA Technologies, Inc.) 2018 Equity Incentive Plan.

Exhibit 10.9.4 CANTALOUPE, INC. 2018 EQUITY INCENTIVE PLAN NOTICE OF RESTRICTED STOCK UNIT GRANT AND RESTRICTED STOCK UNIT AWARD AGREEMENT Cantaloupe, Inc., a Pennsylvania corporation, f/k/a USA Technologies, Inc. (the “Company”), pursuant to its 2018 Equity Incentive Plan (as amended from time to time, the “Plan”) hereby grants to the holder listed below (the “Participant”) an award of restricted

September 10, 2024 EX-4.1

Description of Securities.

Exhibit 4.1 DESCRIPTION OF SECURITIES REGISTERED PURSUANT TO SECTION 12 OF SECURITIES EXCHANGE ACT OF 1934 As of June 30, 2023, Cantaloupe, Inc. has two classes of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”): (1) our Common Stock; (2) our Preferred Stock. Authorized Capital Shares Our authorized capital shares consist of 640,000,00

September 10, 2024 EX-21.1

List of significant subsidiaries of the Company

Exhibit 21.1 SUBSIDIARIES OF THE REGISTRANT Subsidiary State or Province of Incorporation Country of Incorporation Cantaloupe Solutions Canada, Inc. British Columbia Canada Cantaloupe International, Inc. Delaware United States Cantaloupe Systems, Inc. Delaware United States Stitch Networks Corporation Delaware United States USAT Capital Corp, LLC. Pennsylvania United States Three Square Market, In

September 10, 2024 EX-19.1

ing policies and pro

Exhibit 19.1 CANTALOUPE, INC. INSIDER TRADING COMPLIANCE POLICY (As adopted on September 5, 2024) This Insider Trading Compliance Policy (the “Policy”) concerns the handling of material, non-public information relating to Cantaloupe, Inc. (“Cantaloupe”, the “Company”, “our” or “we”) or other companies with which we deal and with the buying and selling of stock and other securities of Cantaloupe an

September 10, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 September 10, 2024 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organizati

September 10, 2024 EX-99.1

Cantaloupe, Inc. Reports Fourth Quarter Fiscal Year 2024 Financial Results Fourth Quarter 2024 Revenue of $72.7 Million, Driven by a 15.4% Year Over Year Growth in Subscription and Transaction Fees Fiscal Year 2024 Revenue of $268.6 Million, a 10.2%

Exhibit 99.1 Cantaloupe, Inc. Reports Fourth Quarter Fiscal Year 2024 Financial Results Fourth Quarter 2024 Revenue of $72.7 Million, Driven by a 15.4% Year Over Year Growth in Subscription and Transaction Fees Fiscal Year 2024 Revenue of $268.6 Million, a 10.2% Year over Year Increase Fiscal Year 2024 U.S. GAAP Net Income Applicable to Common Shares of $11.4 million Fiscal Year 2024 Adjusted EBIT

August 7, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 30, 2023 Date of Report (date of earliest event reported) Cantaloupe, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 30, 2023 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organizatio

May 9, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 9, 2024 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization) (Co

May 9, 2024 EX-99.1

Cantaloupe, Inc. Reports Third Quarter Fiscal Year 2024 Financial Results Third Quarter 2024 Revenue of $67.9 Million, Driven by 15.5% Year Over Year Growth in Subscription and Transaction Fees Third Quarter 2024 Net Income Applicable to Common Share

Exhibit 99.1 Cantaloupe, Inc. Reports Third Quarter Fiscal Year 2024 Financial Results Third Quarter 2024 Revenue of $67.9 Million, Driven by 15.5% Year Over Year Growth in Subscription and Transaction Fees Third Quarter 2024 Net Income Applicable to Common Shares of $4.4 Million and Adjusted EBITDA of $10.2 Million Third Quarter 2024 Gross Margin of 39.6% MALVERN, Pa. - May 9, 2024 - Cantaloupe,

May 9, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact name o

February 21, 2024 SC 13D/A

CTLP / Cantaloupe, Inc. / Hudson Executive Capital LP - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 13) Cantaloupe, Inc. (Name of Issuer) Common Stock, no par value (Title of Class of Securities) 138103106 (CUSIP Number) Douglas L. Braunstein Hudson Executive Capital LP c/o Cadwalader, Wickersham & Taft LLP 200 Liberty Street New York, NY 10281 (212) 521-8

February 9, 2024 SC 13G/A

CTLP / Cantaloupe, Inc. / ABRAMS CAPITAL MANAGEMENT, L.P. - SC 13G/A Passive Investment

SC 13G/A 1 d767697dsc13ga.htm SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* Cantaloupe, Inc. (Name of Issuer) Common Stock, no par value (Title of Class of Securities) 138103106 (CUSIP Number) December 31, 2023 (Date of Event which Requires Filing of this Statement) Check the appropriate bo

February 8, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended December 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact nam

February 8, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 8, 2024 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization

February 8, 2024 EX-99.1

Cantaloupe, Inc. Reports Second Quarter Fiscal Year 2024 Financial Results Second Quarter 2024 Revenue of $65.4 Million, Driven by 15% Year Over Year Growth in Subscription and Transaction Fees Second Quarter 2024 Net Income Applicable to Common Shar

Exhibit 99.1 Cantaloupe, Inc. Reports Second Quarter Fiscal Year 2024 Financial Results Second Quarter 2024 Revenue of $65.4 Million, Driven by 15% Year Over Year Growth in Subscription and Transaction Fees Second Quarter 2024 Net Income Applicable to Common Shares of $3.1 Million and Adjusted EBITDA of $8.5 Million Second Quarter 2024 Gross Margin of 37.2% MALVERN, Pa. - February 8, 2024 - Cantal

February 1, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 1, 2024 Date of Report (date of earliest event reported) Cantaloupe, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 1, 2024 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization

February 1, 2024 EX-99.1

Cantaloupe Acquires CHEQ, a Company Revolutionizing the Sports & Entertainment Fan Experience, Expanding Reach into Stadiums, Venues, Festivals and More Enterprise-grade POS and Mobile-First Ordering Platform Transforming the Way Fans Shop, Order and

Exhibit 99.1 Cantaloupe Acquires CHEQ, a Company Revolutionizing the Sports & Entertainment Fan Experience, Expanding Reach into Stadiums, Venues, Festivals and More Enterprise-grade POS and Mobile-First Ordering Platform Transforming the Way Fans Shop, Order and Pay MALVERN, Pa. – February 1, 2024 – Cantaloupe, Inc. (Nasdaq: CTLP), a leading provider of end-to-end technology solutions for self-se

January 29, 2024 SC 13G/A

CTLP / Cantaloupe, Inc. / BlackRock Inc. Passive Investment

SC 13G/A 1 us1381031061012924.txt us1381031061012924.txt SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No: 2) CANTALOUPE, INC. - (Name of Issuer) Common Stock - (Title of Class of Securities) 138103106 - (CUSIP Number) December 31, 2023 - (Date of Event Which Requires Filing of this Statement) Check the appropriate box t

January 19, 2024 EX-99.3

POWER OF ATTORNEY

EX-99.3 4 d738128dex993.htm EX-99.3 EXHIBIT 3 POWER OF ATTORNEY Know all by these presents, that the undersigned, on behalf of Oakland Hills BV (the “Reporting Person”), in the undersigned’s capacity as a statutory director of Malabar Hill NV, the statutory director of the Reporting Person, hereby constitutes and appoints F. Douglas Raymond as the undersigned’s true and lawful attorney-in-fact to:

January 19, 2024 SC 13G/A

CTLP / Cantaloupe, Inc. / Oakland Hills BV - SC 13G/A Passive Investment

SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 2)* Cantaloupe, Inc. (Name of Issuer) Common stock, no par value (Title of Class of Securities) 138103106 (CUSIP Number) December 31, 2023 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule purs

January 19, 2024 EX-99.1

POWER OF ATTORNEY

EX-99.1 2 d738128dex991.htm EX-99.1 EXHIBIT 1 POWER OF ATTORNEY Know all by these presents, that the undersigned, in the undersigned’s capacity as the executor of the estate of F.H. Fentener van Vlissingen, the former statutory director of Malabar Hill NV, which is the statutory director Oakland Hills BV (the “Reporting Person”), the owner of securities of Cantaloupe, Inc., hereby constitutes and

January 19, 2024 EX-99.4

POWER OF ATTORNEY

EX-99.4 5 d738128dex994.htm EX-99.4 EXHIBIT 4 POWER OF ATTORNEY Know all by these presents, that the undersigned, on behalf of Oakland Hills BV (the “Reporting Person”), in the undersigned’s capacity as a statutory director of Malabar Hill NV, the statutory director of the Reporting Person, hereby constitutes and appoints F. Douglas Raymond as the undersigned’s true and lawful attorney-in-fact to:

January 19, 2024 EX-99.2

POWER OF ATTORNEY

EX-99.2 3 d738128dex992.htm EX-99.2 EXHIBIT 2 POWER OF ATTORNEY Know all by these presents, that the undersigned, on behalf of Oakland Hills BV (the “Reporting Person”), in the undersigned’s capacity as a statutory director of Malabar Hill NV, the statutory director of the Reporting Person, hereby constitutes and appoints F. Douglas Raymond as the undersigned’s true and lawful attorney-in-fact to:

November 9, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact na

November 9, 2023 EX-99.1

Cantaloupe, Inc. Reports First Quarter Fiscal Year 2024 Financial Results First Quarter 2024 Revenue Increased 8% Year-Over-Year, to $62.7 million First Quarter 2024 GAAP Net income applicable to common shares of $1.7 million and Adjusted EBITDA of $

Exhibit 99.1 Cantaloupe, Inc. Reports First Quarter Fiscal Year 2024 Financial Results First Quarter 2024 Revenue Increased 8% Year-Over-Year, to $62.7 million First Quarter 2024 GAAP Net income applicable to common shares of $1.7 million and Adjusted EBITDA of $7.8 million Reiterates Fiscal Year 2024 Guidance MALVERN, Pa. - November 9, 2023 - Cantaloupe, Inc. (Nasdaq: CTLP) (“Cantaloupe” or the “

November 9, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 9, 2023 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization

October 27, 2023 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 ☑ Filed by the Registrant ☐ Filed by a party other than the Registrant CHECK THE APPROPRIATE BOX: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☑ Definitive Proxy State

October 16, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 October 10, 2023 Date of Report (date of earliest event reported) Cantaloupe, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 October 10, 2023 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization

October 16, 2023 EX-16.1

Letter from BDO USA, LLP to the Securities and Exchange Commission dated October 13, 2023

BDO USA refers to BDO USA, P.C., a Virginia professional corporation, also doing business in certain jurisdictions with an alternative identifying abbreviation, such as Corp. or P.S.C. BDO USA, P.C. is the U.S. member of BDO International Limited, a UK company limited by guarantee, and forms part of the international BDO network of independent member firms. BDO is the brand name for the BDO networ

September 25, 2023 EX-4.1

Description of Securities.

Exhibit 4.1 DESCRIPTION OF SECURITIES REGISTERED PURSUANT TO SECTION 12 OF SECURITIES EXCHANGE ACT OF 1934 As of June 30, 2023, Cantaloupe, Inc. has two classes of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”): (1) our Common Stock; (2) our Preferred Stock. Authorized Capital Shares Our authorized capital shares consist of 640,000,00

September 25, 2023 EX-21.1

List of significant subsidiaries of the Company

Exhibit 21.1 SUBSIDIARIES OF THE REGISTRANT Subsidiary State or Province of Incorporation Country of Incorporation Cantaloupe Solutions Canada, Inc. British Columbia Canada Cantaloupe International, Inc. Delaware United States Cantaloupe Systems, Inc. Delaware United States Stitch Networks Corporation Delaware United States USAT Capital Corp, LLC. Pennsylvania United States Three Square Market, In

September 25, 2023 EX-10.9 3

Form of Nonqualified Stock Option Award Agreement under the Cantaloupe, Inc. (f/k/a USA Technologies, Inc.) 2018 Equity Incentive Plan.

Exhibit 10.9.3 CANTALOUPE, INC. 2018 EQUITY INCENTIVE PLAN NOTICE OF NON-QUALIFIED STOCK OPTION GRANT AND NON-QUALIFIED STOCK OPTION AGREEMENT Cantaloupe, Inc., a Pennsylvania corporation, f/k/a USA Technologies, Inc. (the “Company”), pursuant to its 2018 Equity Incentive Plan (as amended from time to time, the “Plan”) hereby grants to the holder listed below (the “Participant”) a non-qualified st

September 25, 2023 EX-10.9 4

Form of Restricted Stock Unit Award Agreement under the Cantaloupe, Inc. (f/k/a USA Technologies, Inc.) 2018 Equity Incentive Plan.

Exhibit 10.9.4 CANTALOUPE, INC. 2018 EQUITY INCENTIVE PLAN NOTICE OF RESTRICTED STOCK UNIT GRANT AND RESTRICTED STOCK UNIT AWARD AGREEMENT Cantaloupe, Inc., a Pennsylvania corporation, f/k/a USA Technologies, Inc. (the “Company”), pursuant to its 2018 Equity Incentive Plan (as amended from time to time, the “Plan”) hereby grants to the holder listed below (the “Participant”) an award of restricted

September 25, 2023 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended June 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact name of registra

September 13, 2023 NT 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 SEC File Number 001-33365 CUSIP NUMBER 138103-106 NOTIFICATION OF LATE FILING (Check one): ☑ Form 10-K ☐ Form 20-F ☐ Form 11-K ☐ Form 10-Q ☐ Form 10-D ☐ Form N-SAR ☐ Form N-CSR For Period Ended: June 30, 2023 ☐ Transition Report on Form 10-K ☐ Transition Report on Form 20-F ☐ Transition Report on Form 11-K ☐ Transi

September 6, 2023 EX-99.1

Cantaloupe, Inc. Reports Fourth Quarter and Fiscal Year 2023 Financial Results Fourth Quarter 2023 Revenue of $64.2 million, an 11% Year over Year Increase Fiscal Year 2023 Revenue of $243.6 million, a 19% Year over Year Increase Fiscal Year 2023 U.S

Exhibit 99.1 Cantaloupe, Inc. Reports Fourth Quarter and Fiscal Year 2023 Financial Results Fourth Quarter 2023 Revenue of $64.2 million, an 11% Year over Year Increase Fiscal Year 2023 Revenue of $243.6 million, a 19% Year over Year Increase Fiscal Year 2023 U.S. GAAP Net Income of $0.01 million Fiscal Year 2023 Adjusted EBITDA of $17.8 million, an 80% Year over Year Increase MALVERN, Pa. - Septe

September 6, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 September 6, 2023 Date of Report (date of earliest event reported) Cantaloupe, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 September 6, 2023 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organizatio

June 6, 2023 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 5, 2023 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization) (C

May 25, 2023 EX-1.01

Exhibit 1.01 – Conflict Minerals Report as required by Items 1.01 and 1.02 of this Form

Exhibit 1.01 Cantaloupe, Inc. Conflict Minerals Report For the Calendar Year Ended December 31, 2022 This Conflict Minerals Report of Cantaloupe, Inc. (this “Report”) has been prepared for the calendar year ended December 31, 2022 pursuant to Section 13(p) of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and Rule 13p-1 and Form SD promulgated under the Exchange Act (collect

May 25, 2023 SD

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM SD Specialized Disclosure Report Commission file number 001-33365 Cantaloupe, Inc. (Exact name of registrant as specified in its charter)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM SD Specialized Disclosure Report Commission file number 001-33365 Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 23-2679963 (State or other jurisdiction of incorporation or organization) (I.R.S. Employer Identification No.) 100 Deerfield Lane, Suite 300, Malvern, Pennsylvania 19355 (A

May 24, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 22, 2023 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exa

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 22, 2023 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization) (C

May 9, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact name o

May 4, 2023 EX-99.1

Cantaloupe, Inc. Reports Third Quarter of Fiscal Year 2023 Financial Results Third Quarter Revenue of $60.4 Million, a 20% Year over Year Increase Third Quarter U.S. GAAP Net Income of $6.7 million Record Adjusted EBITDA of $10.1 Million, a 176% Incr

Exhibit 99.1 Cantaloupe, Inc. Reports Third Quarter of Fiscal Year 2023 Financial Results Third Quarter Revenue of $60.4 Million, a 20% Year over Year Increase Third Quarter U.S. GAAP Net Income of $6.7 million Record Adjusted EBITDA of $10.1 Million, a 176% Increase Compared to Q322 Reiterates Fiscal Year 2023 Guidance MALVERN, Pa. - May 4, 2023 - Cantaloupe, Inc. (Nasdaq: CTLP) (“Cantaloupe” or

May 4, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 4, 2023 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 4, 2023 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization) (Co

March 10, 2023 SC 13G

CTLP / Cantaloupe Inc / Antara Capital LP Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G (Amendment No. ) (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1(b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2(b) Cantaloupe, Inc. (Name of Issuer) Common Stock, no par value (Title of Class of Securities) 138103106 (CUSIP Number) February 28, 2023 (Date

February 9, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 3, 2023 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization

February 9, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended December 31, 2022 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact nam

February 8, 2023 SC 13G/A

CTLP / Cantaloupe, Inc. / Oakland Hills BV - SC 13G/A Passive Investment

SC 13G/A 1 d421909dsc13ga.htm SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 1)* Cantaloupe, Inc. (Name of Issuer) Common stock, no par value (Title of Class of Securities) 138103106 (CUSIP Number) December 31, 2022 (Date of Event which Requires Filing of this Statement) Check the appropriate

February 8, 2023 EX-99.2

POWER OF ATTORNEY

EX-99.2 3 d421909dex992.htm EX-99.2 EXHIBIT 2 POWER OF ATTORNEY Know all by these presents, that the undersigned, on behalf of Oakland Hills BV (the “Reporting Person”), in the undersigned’s capacity as a statutory director of Malabar Hill NV, the statutory director of the Reporting Person, hereby constitutes and appoints F. Douglas Raymond as the undersigned’s true and lawful attorney-in-fact to:

February 8, 2023 EX-99.3

POWER OF ATTORNEY

EX-99.3 4 d421909dex993.htm EX-99.3 EXHIBIT 3 POWER OF ATTORNEY Know all by these presents, that the undersigned, on behalf of Oakland Hills BV (the “Reporting Person”), in the undersigned’s capacity as a statutory director of Malabar Hill NV, the statutory director of the Reporting Person, hereby constitutes and appoints F. Douglas Raymond as the undersigned’s true and lawful attorney-in-fact to:

February 8, 2023 EX-99.1

POWER OF ATTORNEY

EX-99.1 2 d421909dex991.htm EX-99.1 EXHIBIT 1 POWER OF ATTORNEY Know all by these presents, that the undersigned, in the undersigned’s capacity as the executor of the estate of F.H. Fentener van Vlissingen, the former statutory director of Malabar Hill NV, which is the statutory director Oakland Hills BV (the “Reporting Person”), the owner of securities of Cantaloupe, Inc., hereby constitutes and

February 7, 2023 EX-99.1

Cantaloupe, Inc. Reports Second Quarter of Fiscal Year 2023 Financial Results Second Quarter Revenue of $61.3 Million, a 20% Year over Year Increase Reiterates Fiscal Year 2023 Guidance

Exhibit 99.1 Cantaloupe, Inc. Reports Second Quarter of Fiscal Year 2023 Financial Results Second Quarter Revenue of $61.3 Million, a 20% Year over Year Increase Reiterates Fiscal Year 2023 Guidance MALVERN, Pa. - February 7, 2023 - Cantaloupe, Inc. (Nasdaq: CTLP) (“Cantaloupe” or the “Company”), a digital payments and software services company that provides end-to-end technology solutions for sel

February 7, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 7, 2023 Date of Report (date of earliest event reported) Cantaloupe, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 7, 2023 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization

February 1, 2023 SC 13G/A

CTLP / Cantaloupe, Inc. / BlackRock Inc. Passive Investment

SC 13G/A 1 us1381031061020123.txt us1381031061020123.txt SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No: 1) CANTALOUPE, INC. - (Name of Issuer) Common Stock - (Title of Class of Securities) 138103106 - (CUSIP Number) December 31, 2022 - (Date of Event Which Requires Filing of this Statement) Check the appropriate box t

January 25, 2023 EX-2

IDENTIFICATION AND CLASSIFICATION OF MEMBERS OF THE GROUP

EX-2 3 ex2.htm EXHIBIT 2 EXHIBIT 2 IDENTIFICATION AND CLASSIFICATION OF MEMBERS OF THE GROUP ARDSLEY ADVISORY PARTNERS LP ARDSLEY ADVISORY PARTNERS GP LLC ARDSLEY PARTNERS I GP LLC PHILLIP J. HEMPLEMAN ARDSLEY PARTNERS ADVANCED HEALTHCARE FUND, L.P.

January 25, 2023 EX-1

JOINT FILING AGREEMENT

EX-1 2 ex1.htm EXHIBIT 1 EXHIBIT 1 JOINT FILING AGREEMENT In accordance with Rule 13d-1(f) under the Securities Exchange Act of 1934, as amended, the persons named below agree to the joint filing on behalf of each of them of this Schedule 13G/A (including amendments thereto) with respect to the Common Stock of Cantaloupe, Inc. and further agree that this Joint Filing Agreement be included as an Ex

January 25, 2023 SC 13G/A

CTLP / Cantaloupe, Inc. / ARDSLEY ADVISORY PARTNERS LP - SC 13G/A Passive Investment

SC 13G/A 1 cantaloupe13ga1.htm SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A (Amendment No. 1) Under the Securities Exchange Act of 1934 Cantaloupe, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 138103106 (CUSIP Number) December 31, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designa

January 13, 2023 EX-99.1

JOINT FILING AGREEMENT

EX-99.1 2 d270795dex991.htm EX-99.1 Exhibit 99.1 JOINT FILING AGREEMENT This Joint Filing Agreement is by and among Abrams Capital Partners II, L.P., Abrams Capital, LLC, Abrams Capital Management, LLC, Abrams Capital Management, L.P. and David Abrams (collectively, the “Filers”). Each of the Filers may be required to file with the United States Securities and Exchange Commission a statement on Sc

January 13, 2023 SC 13D/A

CTLP / Cantaloupe, Inc. / Legion Partners Asset Management, LLC - AMENDMENT NO. 3 TO THE SCHEDULE 13D Activist Investment

SC 13D/A 1 sc13da30905000901132023.htm AMENDMENT NO. 3 TO THE SCHEDULE 13D UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-101) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO § 240.13d-1(a) AND AMENDMENTS THERETO FILED PURSUANT TO § 240.13d-2(a) (Amendment No. 3)1 Cantaloupe, Inc. (Name of Issuer) Preferred Stock, no par value (Title of Cl

January 13, 2023 SC 13G

CTLP / Cantaloupe, Inc. / Abrams Capital Partners II, L.P. - SC 13G Passive Investment

SC 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 Cantaloupe, Inc. (Name of Issuer) Common Stock, no par value (Title of Class of Securities) 138103106 (CUSIP Number) January 5, 2023 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedu

December 23, 2022 S-8

As filed with the Securities and Exchange Commission on December 23, 2022

S-8 As filed with the Securities and Exchange Commission on December 23, 2022 Registration No.

December 23, 2022 EX-FILING FEES

Filing Fee Table

EX-FILING FEES 4 d426821dexfilingfees.htm EX-FILING FEES Exhibit 107 Calculation of Filing Fee Table FORM S-8 (Form Type) CANTALOUPE, INC. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered (1)(2) Proposed Maximum Aggregate Offering Price Per Share (3) Proposed Maximum Aggregate Offer

December 5, 2022 8-K

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 December 1, 2022 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization

December 5, 2022 EX-10.1

First Amendment to Amended and Restated Credit Agreement, by and among the Company, its subsidiaries, and JPMorgan Bank, N.A., dated December 1, 2022 (incorporated by reference to Exhibit 10.1 to From 8-K filed December 5, 2022).

FIRST AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT FIRST AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT (this ?Amendment?) dated as of December 1, 2022 by and among CANTALOUPE, INC.

December 5, 2022 EX-99.1

Cantaloupe Acquires Three Square Market (32M), Accelerating the Company’s Micro Market Presence and International Expansion Combined Company Offers Full Range of Self-Service Kiosk, Payment, and Software Solutions to the Fast-Growing Micro Market Ind

Cantaloupe Acquires Three Square Market (32M), Accelerating the Company?s Micro Market Presence and International Expansion Combined Company Offers Full Range of Self-Service Kiosk, Payment, and Software Solutions to the Fast-Growing Micro Market Industry 32M?s Presence in Europe Accelerates Expansion of Cantaloupe?s Geographic Footprint Immediately Accretive to Cantaloupe?s Growth, Margins and Profitability MALVERN, Pa.

December 2, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 30, 2022 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organizatio

November 22, 2022 SC 13D/A

CTLP / Cantaloupe, Inc. / Legion Partners Asset Management, LLC - AMENDMENT NO. 2 TO THE SCHEDULE 13D Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-101) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO ? 240.13d-1(a) AND AMENDMENTS THERETO FILED PURSUANT TO ? 240.13d-2(a) (Amendment No. 2)1 Cantaloupe, Inc. (Name of Issuer) Preferred Stock, no par value (Title of Class of Securities) 138103205 (CUSIP Number) CHRISTOPHER S. KIPER LEGION PAR

November 22, 2022 EX-99.1

JOINT FILING AGREEMENT

Exhibit 99.1 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k)(1)(iii) under the Securities Exchange Act of 1934, as amended, the persons named below agree to the joint filing on behalf of each of them of a Statement on Schedule 13D (including amendments thereto) with respect to the shares of Preferred Stock, no par value per share, of Cantaloupe, Inc.. This Joint Filing Agreement shall be f

November 9, 2022 EX-10.8 2

Form of Nonqualified Stock Option Award Agreement under the Cantaloupe, Inc. (f/k/a USA Technologies, Inc.) 2018 Equity Incentive Plan.

Exhibit 10.8.2 CANTALOUPE, INC. 2018 EQUITY INCENTIVE PLAN NOTICE OF NON-QUALIFIED STOCK OPTION GRANT AND NON-QUALIFIED STOCK OPTION AGREEMENT Cantaloupe, Inc., a Pennsylvania corporation, f/k/a USA Technologies, Inc. (the ?Company?), pursuant to its 2018 Equity Incentive Plan (as amended from time to time, the ?Plan?) hereby grants to the holder listed below (the ?Participant?) a non-qualified st

November 9, 2022 EX-4.1

Description of Securities.

Exhibit 4.1 DESCRIPTION OF SECURITIES REGISTERED PURSUANT TO SECTION 12 OF SECURITIES EXCHANGE ACT OF 1934 As of June 30, 2022, Cantaloupe, Inc. has two classes of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the ?Exchange Act?): (1) our Common Stock; (2) our Preferred Stock. Authorized Capital Shares Our authorized capital shares consist of 640,000,00

November 9, 2022 EX-21.1

List of significant subsidiaries of the Company

Exhibit 21.1 SUBSIDIARIES OF THE REGISTRANT Subsidiary State or Province of Incorporation Country of Incorporation Cantaloupe Solutions Canada, Inc. British Columbia Canada Cantaloupe International, Inc. Delaware United States Cantaloupe Systems, Inc. Delaware United States Stitch Networks Corporation Delaware United States USAT Capital Corp, LLC. Pennsylvania United States

November 9, 2022 EX-10.8 3

Form of Restricted Stock Unit Award Agreement under the Cantaloupe, Inc. (f/k/a USA Technologies, Inc.) 2018 Equity Incentive Plan.

Exhibit 10.8.3 CANTALOUPE, INC. 2018 EQUITY INCENTIVE PLAN NOTICE OF RESTRICTED STOCK UNIT GRANT AND RESTRICTED STOCK UNIT AWARD AGREEMENT Cantaloupe, Inc., a Pennsylvania corporation, f/k/a USA Technologies, Inc. (the ?Company?), pursuant to its 2018 Equity Incentive Plan (as amended from time to time, the ?Plan?) hereby grants to the holder listed below (the ?Participant?) an award of restricted

November 9, 2022 10-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A Amendment No. 1

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A Amendment No. 1 ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended June 30, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exac

November 9, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact na

November 7, 2022 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 7, 2022 Date of Report (date of earliest event reported) Cantaloupe, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 7, 2022 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization

November 7, 2022 EX-99.1

Cantaloupe, Inc. Reports First Quarter Fiscal Year 2023 Results First Quarter Revenue of $57.8 Million, a 26% Year over Year Increase Reiterates Fiscal Year 2023 Guidance

Exhibit 99.1 Cantaloupe, Inc. Reports First Quarter Fiscal Year 2023 Results First Quarter Revenue of $57.8 Million, a 26% Year over Year Increase Reiterates Fiscal Year 2023 Guidance MALVERN, Pa. - November 7, 2022 - Cantaloupe, Inc. (Nasdaq: CTLP) (“Cantaloupe” or the “Company”), a digital payments and software services company that provides end-to-end technology solutions for the unattended ret

October 28, 2022 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant  ☐ Check the appropriate box:  ☐ Preliminary Proxy Statement  ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ D

October 19, 2022 EX-21.1

List of significant subsidiaries of the Company

Exhibit 21.1 SUBSIDIARIES OF THE REGISTRANT Subsidiary State or Province of Incorporation Country of Incorporation Cantaloupe Solutions Canada, Inc. British Columbia Canada Cantaloupe International, Inc. Delaware United States Cantaloupe Systems, Inc. Delaware United States Stitch Networks Corporation Delaware United States USAT Capital Corp, LLC. Pennsylvania United States

October 19, 2022 EX-10.8 2

Form of Nonqualified Stock Option Award Agreement under the Cantaloupe, Inc. (f/k/a USA Technologies, Inc.) 2018 Equity Incentive Plan.

Exhibit 10.8.2 CANTALOUPE, INC. 2018 EQUITY INCENTIVE PLAN NOTICE OF NON-QUALIFIED STOCK OPTION GRANT AND NON-QUALIFIED STOCK OPTION AGREEMENT Cantaloupe, Inc., a Pennsylvania corporation, f/k/a USA Technologies, Inc. (the ?Company?), pursuant to its 2018 Equity Incentive Plan (as amended from time to time, the ?Plan?) hereby grants to the holder listed below (the ?Participant?) a non-qualified st

October 19, 2022 EX-4.1

Description of Securities

Exhibit 4.1 DESCRIPTION OF SECURITIES REGISTERED PURSUANT TO SECTION 12 OF SECURITIES EXCHANGE ACT OF 1934 As of June 30, 2022, Cantaloupe, Inc. has two classes of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the ?Exchange Act?): (1) our Common Stock; (2) our Preferred Stock. Authorized Capital Shares Our authorized capital shares consist of 640,000,00

October 19, 2022 EX-10.8 3

Form of Restricted Stock Unit Award Agreement under the Cantaloupe, Inc. (f/k/a USA Technologies, Inc.) 2018 Equity Incentive Plan.

Exhibit 10.8.3 CANTALOUPE, INC. 2018 EQUITY INCENTIVE PLAN NOTICE OF RESTRICTED STOCK UNIT GRANT AND RESTRICTED STOCK UNIT AWARD AGREEMENT Cantaloupe, Inc., a Pennsylvania corporation, f/k/a USA Technologies, Inc. (the ?Company?), pursuant to its 2018 Equity Incentive Plan (as amended from time to time, the ?Plan?) hereby grants to the holder listed below (the ?Participant?) an award of restricted

October 19, 2022 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended June 30, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact name of registra

September 30, 2022 EX-99.1

Cantaloupe, Inc. Receives Nasdaq Notification Of Non-Compliance With Listing Rule 5250(c)(1)

Cantaloupe, Inc. Receives Nasdaq Notification Of Non-Compliance With Listing Rule 5250(c)(1) MALVERN, Pa., September 30, 2022 - Cantaloupe, Inc. (Nasdaq: CTLP) (?Cantaloupe? or the ?Company?), a digital payments and software services company that provides end-to-end technology solutions for the unattended retail market, today announced that it has received a notice (the "Notice") from the Listing

September 30, 2022 8-K

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 September 30, 2022 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organizati

September 28, 2022 EX-99.1

Cantaloupe, Inc. to Delay Form 10-K Filing for Fiscal Year 2022

Cantaloupe, Inc. to Delay Form 10-K Filing for Fiscal Year 2022 MALVERN, Pa., September 28, 2022 - Cantaloupe, Inc. (Nasdaq: CTLP) (?Cantaloupe? or the ?Company?), a digital payments and software services company that provides end-to-end technology solutions for the unattended retail market, today announced that it will not timely file its Annual Report on Form 10-K for the fiscal year ended June

September 28, 2022 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 September 28, 2022 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organizati

September 14, 2022 NT 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 SEC File Number 001-33365 CUSIP NUMBER 138103-106 NOTIFICATION OF LATE FILING (Check one): ? Form 10-K ? Form 20-F ? Form 11-K ? Form 10-Q ? Form 10-D ? Form N-SAR ? Form N-CSR For Period Ended: June 30, 2022 ? Transition Report on Form 10-K ? Transition Report on Form 20-F ? Transition Report on Form 11-K ? Transi

September 8, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 September 8, 2022 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organizatio

September 8, 2022 EX-10.1

Separation and Transition Agreement, by and between Cantaloupe, Inc. and Sean Feeney (incorporated by reference to Exhibit 10.1 to the Form 8-K filed September 8, 2022).

SEPARATION AND TRANSITION AGREEMENT THIS SEPARATION AND TRANSITION AGREEMENT (the ?Agreement?) is entered into by and between Cantaloupe, Inc.

September 8, 2022 EX-10.2

Promotion Letter, between Cantaloupe, Inc. and Ravi Venkatesan (incorporated by reference to Exhibit 10.2 to the Form 8-K filed September 8, 2022).

September 8, 2022 Re: Promotion Letter Dear Ravi: Through this letter, Cantaloupe, Inc.

September 8, 2022 EX-99.1

Cantaloupe, Inc. Reports Record Revenue for the Fourth Quarter and Fiscal Year 2022 Fourth Quarter Revenue Increased 18% Year over Year to $58 million Fiscal Year 2022 Revenue Increased 23% Year over Year to $205 million

Cantaloupe, Inc. Reports Record Revenue for the Fourth Quarter and Fiscal Year 2022 Fourth Quarter Revenue Increased 18% Year over Year to $58 million Fiscal Year 2022 Revenue Increased 23% Year over Year to $205 million MALVERN, Pa. - September 8, 2022 - Cantaloupe, Inc. (Nasdaq: CTLP) (?Cantaloupe? or the ?Company?), a digital payments and software services company that provides end-to-end techn

July 20, 2022 EX-99.1

POWER OF ATTORNEY

EXHIBIT 1 POWER OF ATTORNEY Know all by these presents, that the undersigned, on behalf of Oakland Hills BV (the ?Reporting Person?), in the undersigned?s capacity as a statutory director of Malabar Hill NV, the statutory director of the Reporting Person, hereby constitutes and appoints F.

July 20, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 July 20, 2022 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization) (

July 20, 2022 SC 13G

CTLP / Cantaloupe, Inc. / Oakland Hills BV - SC 13G Passive Investment

SC 13G 1 d375471dsc13g.htm SC 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Cantaloupe, Inc. (Name of Issuer) Common stock, no par value (Title of Class of Securities) 138103106 (CUSIP Number) July 13, 2022 (Date of Event which Requires Filing of this Statement) Check the appropriate box to desig

May 26, 2022 SD

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM SD Specialized Disclosure Report Commission file number 001-33365 Cantaloupe, Inc. (Exact name of registrant as specified in its charter)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM SD Specialized Disclosure Report Commission file number 001-33365 Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 23-2679963 (State or other jurisdiction of incorporation or organization) (I.R.S. Employer Identification No.) 100 Deerfield Lane, Suite 300, Malvern, Pennsylvania 19355 (A

May 26, 2022 EX-1.01

Exhibit 1.01 – Conflict Minerals Report as required by Items 1.01 and 1.02 of this Form

EX-1.01 2 formsd-exhibit101x12312021.htm EX-1.01 Exhibit 1.01 Cantaloupe, Inc. Conflict Minerals Report For the Calendar Year Ended December 31, 2021 This Conflict Minerals Report of Cantaloupe, Inc. (this “Report”) has been prepared for the calendar year ended December 31, 2021 pursuant to Section 13(p) of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and Rule 13p-1 and Fo

May 6, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact name o

May 5, 2022 EX-99.1

Cantaloupe, Inc. Reports Third Quarter 2022 Financial Results, Which Includes Record Transaction Fee Revenue

Cantaloupe, Inc. Reports Third Quarter 2022 Financial Results, Which Includes Record Transaction Fee Revenue MALVERN, Pa. - May 5, 2022 - Cantaloupe, Inc. (Nasdaq: CTLP) (?Cantaloupe? or the ?Company?), a leading company in digital payments and software services, that provides end-to-end technology solutions for the convenience retail market, today reported results for the fiscal year 2022 third q

May 5, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 5, 2022 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization) (Co

March 24, 2022 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 March 17, 2022 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization)

March 24, 2022 EX-10.1

Credit Agreement, by and among the Company, its subsidiaries, and JPMorgan Chase Bank, N.A., dated March 17, 2022.

Execution Version #153723541v10 AMENDED AND RESTATED CREDIT AGREEMENT dated as of March 17, 2022, among CANTALOUPE, INC.

February 16, 2022 SC 13D/A

CTLP / Cantaloupe, Inc. / Antara Capital LP Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 8)* Cantaloupe, Inc. (Name of Issuer) Common Stock, no par value (Title of Class of Securities) 90328S500 (CUSIP Number) Lance Kravitz Antara Capital LP 55 Hudson Yards, 47th Floor, Suite C New York, New York 10001 (646) 762 8591 (Name, Address and Telephone

February 8, 2022 EX-1

JOINT FILING AGREEMENT

EXHIBIT 1 JOINT FILING AGREEMENT In accordance with Rule 13d-1(f) under the Securities Exchange Act of 1934, as amended, the persons named below agree to the joint filing on behalf of each of them of this Schedule 13G (including amendments thereto) with respect to the Common Stock of Cantaloupe, Inc.

February 8, 2022 EX-2

IDENTIFICATION AND CLASSIFICATION OF MEMBERS OF THE GROUP

EXHIBIT 2 IDENTIFICATION AND CLASSIFICATION OF MEMBERS OF THE GROUP ARDSLEY ADVISORY PARTNERS LP ARDSLEY ADVISORY PARTNERS GP LLC ARDSLEY PARTNERS I GP LLC PHILLIP J. HEMPLEMAN ARDSLEY PARTNERS ADVANCED HEALTHCARE FUND, L.P.

February 8, 2022 SC 13G

CTLP / Cantaloupe, Inc. / ARDSLEY ADVISORY PARTNERS LP - SC 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 Cantaloupe, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 138103106 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedule is filed: x Rule

February 4, 2022 EX-3.1

Amended and Restated Articles of Incorporation (incorporated by reference to Exhibit 3.1 to Form 10-Q filed on February 4, 2022).

CANTALOUPE, INC. AMENDED AND RESTATED ARTICLES OF INCORPORATION, AS AMENDED THROUGH APRIL 15, 2021 1. The name of the corporation is CANTALOUPE, INC. 2. The address of the corporation?s current registered office in the Commonwealth is 100 Deerfield Lane, Suite 140, Malvern, PA 19355, Montgomery County. 3. The corporation is incorporated under the Business Corporation Law of 1988. 4. Capital Stock.

February 4, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended December 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact nam

February 4, 2022 SC 13G

CTLP / Cantaloupe, Inc. / BlackRock Inc. Passive Investment

us1381031061020422.txt SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No: ) CANTALOUPE, INC. - (Name of Issuer) Common Stock - (Title of Class of Securities) 138103106 - (CUSIP Number) December 31, 2021 - (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to wh

February 3, 2022 EX-10.4

Employment Agreement, between Cantaloupe, Inc. and Scott Stewart (incorporated by reference to Exhibit 10.4 to Form 8-K filed February 3, 2022)

Exhibit 10.4 EMPLOYMENT AGREEMENT This Employment Agreement (?Agreement?) is hereby made between Cantaloupe, Inc. a Pennsylvania corporation (?Company?), and Scott Stewart (?Executive?). Each of Company and Executive is a ?Party? to this Agreement, and collectively are the ?Parties? to this Agreement. RECITALS A.The Company is engaged in the business of cashless payments processing (?Business?). B

February 3, 2022 EX-10.5

Employment Agreement, between Cantaloupe, Inc. and Ravi Venkatesan (incorporated by reference to Exhibit 10.5 to Form 8-K filed February 3, 2022).

Exhibit 10.5 EMPLOYMENT AGREEMENT This Employment Agreement (?Agreement?) is hereby made between Cantaloupe, Inc. a Pennsylvania corporation (?Company?), and Ravi Venkatesan (?Executive?). Each of Company and Executive is a ?Party? to this Agreement, and collectively are the ?Parties? to this Agreement. RECITALS A.The Company is engaged in the business of cashless payments processing (?Business?).

February 3, 2022 EX-99.1

Third Consecutive Quarter of Record Transaction Fees Revenue Reaffirms Fiscal Year 2022 Outlook

Exhibit 99.1 Cantaloupe, Inc. Reports Record Quarterly Revenue for Second Quarter 2022 Third Consecutive Quarter of Record Transaction Fees Revenue Reaffirms Fiscal Year 2022 Outlook MALVERN, Pa. - February 3, 2022 - Cantaloupe, Inc. (Nasdaq: CTLP) (?Cantaloupe? or the ?Company?), a leading company in digital payments and software services, that provides end-to-end technology solutions for the una

February 3, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 3, 2022 Date of Report (date of earliest event reported) Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization

February 3, 2022 EX-10.3

Separation and Transition Agreement, by and between Cantaloupe, Inc. and R. Wayne Jackson (incorporated by reference to Exhibit 10.3 to Form 8-K filed February 3, 2022).

Exhibit 10.3 SEPARATION AND TRANSITION AGREEMENT THIS SEPARATION AND TRANSITION AGREEMENT (the ?Agreement?) is entered into by and between Cantaloupe, Inc. (f/k/a USA Technologies, Inc.), a Pennsylvania corporation (the ?Company?), and R. Wayne Jackson (?Employee?), as of February 4, 2022. WHEREAS, Employee is the Company?s Chief Financial Officer; WHEREAS, Employee?s employment with the Company w

January 25, 2022 EX-99.1

POWER OF ATTORNEY

EXHIBIT 1 POWER OF ATTORNEY Know all by these presents, that the undersigned, on behalf of Oakland Hills BV (the ?Reporting Person?), in the undersigned?s capacity as a statutory director of Malabar Hill NV, the statutory director of the Reporting Person, hereby constitutes and appoints F.

January 25, 2022 SC 13G/A

CTLP / Cantaloupe, Inc. / Oakland Hills BV - SCHEDULE 13G AMENDMENT NO. 5 Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 5)* Cantaloupe, Inc. (Name of Issuer) Common stock, no par value (Title of Class of Securities) 138103106 (CUSIP Number) December 31, 2021 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to w

November 12, 2021 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): November 10, 2021 CANTALOUPE, INC. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organizati

November 5, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact na

November 4, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): November 4, 2021 CANTALOUPE, INC. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organizatio

November 4, 2021 EX-99.1

Cantaloupe, Inc. Reports First Quarter Fiscal Year 2022 Results First Quarter Revenue Increased 24% Year over Year; Record Transaction Fee Revenue of $26.4 Million Reaffirms Fiscal Year 2022 Outlook

Exhibit 99.1 Cantaloupe, Inc. Reports First Quarter Fiscal Year 2022 Results First Quarter Revenue Increased 24% Year over Year; Record Transaction Fee Revenue of $26.4 Million Reaffirms Fiscal Year 2022 Outlook MALVERN, Pa. - November 4, 2021 - Cantaloupe, Inc. (Nasdaq: CTLP) (?Cantaloupe? or the ?Company?), a digital payments and software services company that provides end-to-end technology solu

October 6, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): October 5, 2021 CANTALOUPE, INC. (Exact Name of Registrant as Specified in Its Charter) Pennsylvania 001-33365 23-2679963 (State or Other Jurisdiction of Incorporation) (Commission Fi

October 1, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the app

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy State

October 1, 2021 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ? ? ? Filed by a Party other than the Registrant ? ? ?? Check the appropriate box: ?? ? ? Preliminary Proxy Statement ?? ? ? Confidential, for Use of the Commission Only (as permitted by Rule

September 3, 2021 EX-10.28

Settlement Agreement and Mutual General Release, by and between Michael Wasserfuhr, Sean Feeney, Douglas Bergeron, and the Company, dated as of March 27, 2021.

Exhibit 10.28 SETTLEMENT AGREEMENT AND MUTUAL GENERAL RELEASE This Settlement Agreement and Mutual General Release (the ?Agreement?) is made and entered into by and among Michael Wasserfuhr (?Wasserfuhr?), on the one hand, and USA Technologies, Inc., Sean Feeney (?Feeney?), and Douglas Bergeron (?Bergeron?), on the other hand. When used herein, the term ?USAT? shall mean and include USA Technologi

September 3, 2021 EX-10.10.2

Form of Nonqualified Stock Option Award Agreement under the Cantaloupe, Inc. (f/k/a USA Technologies, Inc.) 2018 Equity Incentive Plan.

Exhibit 10.10.2 CANTALOUPE, INC. 2018 EQUITY INCENTIVE PLAN NOTICE OF NON-QUALIFIED STOCK OPTION GRANT AND NON-QUALIFIED STOCK OPTION AGREEMENT Cantaloupe, Inc., a Pennsylvania corporation, f/k/a USA Technologies, Inc. (the ?Company?), pursuant to its 2018 Equity Incentive Plan (as amended from time to time, the ?Plan?) hereby grants to the holder listed below (the ?Participant?) a non-qualified s

September 3, 2021 EX-4.1

Description of Securities

Exhibit 4.1 DESCRIPTION OF SECURITIES REGISTERED PURSUANT TO SECTION 12 OF SECURITIES EXCHANGE ACT OF 1934 As of June 30, 2021, Cantaloupe, Inc. has two classes of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the ?Exchange Act?): (1) our Common Stock; (2) our Preferred Stock. Authorized Capital Shares Our authorized capital shares consist of 640,000,00

September 3, 2021 EX-10.10.3

Form of Restricted Stock Unit Award Agreement under the Cantaloupe, Inc. (f/k/a USA Technologies, Inc.) 2018 Equity Incentive Plan.

Exhibit 10.10.3 CANTALOUPE, INC. 2018 EQUITY INCENTIVE PLAN NOTICE OF RESTRICTED STOCK UNIT GRANT AND RESTRICTED STOCK UNIT AWARD AGREEMENT Cantaloupe, Inc., a Pennsylvania corporation, f/k/a USA Technologies, Inc. (the ?Company?), pursuant to its 2018 Equity Incentive Plan (as amended from time to time, the ?Plan?) hereby grants to the holder listed below (the ?Participant?) an award of restricte

September 3, 2021 EX-21.1

List of significant subsidiaries of the Company

Exhibit 21.1 SUBSIDIARIES OF THE REGISTRANT Subsidiary State or Province of Incorporation Country of Incorporation Cantaloupe Solutions Canada, Inc. British Columbia Canada Cantaloupe International, Inc. Delaware United States Cantaloupe Systems, Inc. Delaware United States Stitch Networks Corporation Delaware United States USAT Capital Corp, LLC. Pennsylvania United States

September 3, 2021 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended June 30, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact name of registra

September 2, 2021 EX-99.1

Cantaloupe, Inc. Reports Fourth Quarter and Fiscal Year 2021 Results Record Fourth Quarter Revenue increased 50% Year over Year Company Provides Fiscal Year 2022 Outlook

Exhibit 99.1 Cantaloupe, Inc. Reports Fourth Quarter and Fiscal Year 2021 Results Record Fourth Quarter Revenue increased 50% Year over Year Company Provides Fiscal Year 2022 Outlook MALVERN, Pa - September 2, 2021 - Cantaloupe, Inc. (Nasdaq: CTLP) (?Cantaloupe? or the ?Company?), a digital payments and software services company that provides end-to-end technology solutions for the unattended reta

September 2, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): September 2, 2021 CANTALOUPE, INC. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organizati

August 10, 2021 EX-3.1

Second Amended and Restated Bylaws (incorporated by reference to Exhibit 3.1 to Form 8-K filed on August 10, 2021).

Exhibit 3.1 SECOND AMENDED AND RESTATED BYLAWS OF CANTALOUPE, INC. (a Pennsylvania corporation) (as amended August 6, 2021) Cantaloupe, Inc., pursuant to the applicable provisions of the Pennsylvania Business Corporation Law, hereby adopts these Second Amended and Restated Bylaws, which restate, amend and supersede the bylaws of the Corporation, as previously amended and restated, in their entiret

August 10, 2021 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): August 6, 2021 CANTALOUPE, INC. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization)

June 3, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): June 1, 2021 CANTALOUPE, INC. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization) (

June 3, 2021 EX-10.1

Separation and Transition Agreement, by and between James Pollock and Cantaloupe, Inc., dated as of June 1, 2021.

Exhibit 10.1 SEPARATION AND TRANSITION AGREEMENT THIS SEPARATION AND TRANSITION AGREEMENT (the ?Agreement?) is entered into by and between Cantaloupe, Inc. (f/k/a USA Technologies, Inc.), a Pennsylvania corporation (the ?Company?), and James M. Pollock (?Employee?), as of June 1, 2021. WHEREAS, Employee previously served as the Company?s Chief Compliance Officer; WHEREAS, Employee?s employment wit

May 27, 2021 EX-1.01

Exhibit 1.01 – Conflict Minerals Report as required by Items 1.01 and 1.02 of this Form

Exhibit 1.01 Cantaloupe, Inc. Conflict Minerals Report For the Calendar Year Ended December 31, 2020 This Conflict Minerals Report of Cantaloupe, Inc. (this ?Report?) has been prepared for the calendar year ended December 31, 2020 pursuant to Section 13(p) of the Securities Exchange Act of 1934, as amended (the ?Exchange Act?), and Rule 13p-1 and Form SD promulgated under the Exchange Act (collect

May 27, 2021 SD

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM SD Specialized Disclosure Report Commission file number 001-33365 Cantaloupe, Inc. (Exact name of registrant as specified in its charter)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM SD Specialized Disclosure Report Commission file number 001-33365 Cantaloupe, Inc. (Exact name of registrant as specified in its charter) Pennsylvania 23-2679963 (State or other jurisdiction of incorporation or organization) (I.R.S. Employer Identification No.) 100 Deerfield Lane, Suite 300, Malvern, Pennsylvania 19355 (A

May 13, 2021 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): May 13, 2021 CANTALOUPE, INC. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization) (

May 7, 2021 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 (d) OF THE EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-33365 Cantaloupe, Inc. (Exact name o

May 6, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): May 6, 2021 CANTALOUPE, INC. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization) (C

May 6, 2021 EX-99.1

Cantaloupe, Inc. Reports Third Quarter Fiscal Year 2021 Results

Exhibit 99.1 Cantaloupe, Inc. Reports Third Quarter Fiscal Year 2021 Results MALVERN, Pa ? May 6, 2021 - Cantaloupe, Inc., (NASDAQ:CTLP) (?CTLP? or the ?Company?), a digital payments and software services company that provides end-to-end technology solutions for the unattended retail market, today reported results for the fiscal year 2021 third quarter. ?We are pleased with our financial results f

April 15, 2021 8-K

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): April 15, 2021 CANTALOUPE, INC. (Exact name of registrant as specified in its charter) Pennsylvania 001-33365 23-2679963 (State or other jurisdiction of incorporation or organization)

April 14, 2021 424B3

USA TECHNOLOGIES, INC. Common Stock Preferred Stock Debt Securities Subscription Rights Offered by the Company Shares of Common Stock Offered by Selling Shareholders

424B3 1 nt10022721x2424b3.htm 424B3 TABLE OF CONTENTS Filed pursuant to Rule 424(b)(3) Commission File No. 333-255040 PROSPECTUS   USA TECHNOLOGIES, INC. $100,000,000 Common Stock Preferred Stock Debt Securities Warrants Units Subscription Rights Offered by the Company and 5,730,000 Shares of Common Stock Offered by Selling Shareholders This prospectus relates to common stock, preferred stock, deb

April 12, 2021 LETTER

LETTER

United States securities and exchange commission logo April 12, 2021 Sean Feeney Chief Executive Officer USA Technologies, Inc.

April 12, 2021 TEXT-EXTRACT

TEXT-EXTRACT

United States securities and exchange commission logo April 12, 2021 Sean Feeney Chief Executive Officer USA Technologies, Inc.

April 12, 2021 CORRESP

April 12, 2021

April 12, 2021 Via EDGAR United States Securities and Exchange Commission Division of Corporate Finance Office of Technology Washington, D.

April 5, 2021 EX-4.3

USA TECHNOLOGIES, INC. [ ] DATED AS OF , 20 SENIOR DEBT SECURITIES USA TECHNOLOGIES, INC. RECONCILIATION AND TIE BETWEEN TRUST INDENTURE ACT OF 1939, AS AMENDED, AND INDENTURE, DATED AS OF , 20

EXHIBIT 4.3 USA TECHNOLOGIES, INC. AND [ ] Trustee INDENTURE DATED AS OF , 20 SENIOR DEBT SECURITIES USA TECHNOLOGIES, INC. RECONCILIATION AND TIE BETWEEN TRUST INDENTURE ACT OF 1939, AS AMENDED, AND INDENTURE, DATED AS OF , 20 TRUST INDENTURE ACT SECTION INDENTURE SECTION Section 310(a)(1) 6.9 (a)(2) 6.9 (a)(3) Not Applicable (a)(4) Not Applicable (a)(5) 6.9 (b) 6.8 Section 311 6.13 Section 312(a

April 5, 2021 EX-4.4

USA TECHNOLOGIES, INC. [ ] DATED AS OF , 20 SUBORDINATED DEBT SECURITIES USA TECHNOLOGIES, INC. RECONCILIATION AND TIE BETWEEN TRUST INDENTURE ACT OF 1939, AS AMENDED, AND INDENTURE, DATED AS OF , 20

EXHIBIT 4.4 USA TECHNOLOGIES, INC. AND [ ] Trustee INDENTURE DATED AS OF , 20 SUBORDINATED DEBT SECURITIES USA TECHNOLOGIES, INC. RECONCILIATION AND TIE BETWEEN TRUST INDENTURE ACT OF 1939, AS AMENDED, AND INDENTURE, DATED AS OF , 20 TRUST INDENTURE ACT SECTION INDENTURE SECTION Section 310(a)(1) 6.9 (a)(2) 6.9 (a)(3) Not Applicable (a)(4) Not Applicable (a)(5) 6.9 (b) 6.8 Section 311 6.13 Section

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