Company: CTLPP
Filing Date: 2025-07-24
Form Type: DEFM14A
Source: 0001140361-25-027048
Chunk: 0

Company: CANTALOUPE, INC.
Filing Date: 2025-07-24
Form: DEFM14A
Chunk 0
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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)) |

| ☒ | Definitive Proxy Statement |

| ☐ | Definitive Additional Materials |

| ☐ | Soliciting Material under §240.14a-12 |

Cantaloupe, Inc. (Name of Registrant as Specified In Its Charter) N/A (Name of Person(s) Filing Proxy Statement, if other than the Registrant) Payment of Filing Fee (Check the appropriate box):

| ☐ | No fee required |

| ☒ | Fee paid previously with preliminary materials |

| ☐ | Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11 |

#### TABLE OF CONTENTS
Letter to Cantaloupe’s Shareholders

from Cantaloupe’s Chief Executive Officer and Director

and Cantaloupe’s Chairman of the Board of Directors

#### Dear Fellow Shareholders,
**You are cordially invited to attend a special meeting (which, including any adjournments or postponements thereof, we refer to as the “Special Meeting”) of the shareholders of Cantaloupe, Inc. (which we refer to as “Cantaloupe”) to be held on September 4, 2025, at 8:00 a.m., Eastern time, virtually at www.virtualshareholdermeeting.com/CTLP2025SM.

At the Special Meeting, Cantaloupe will ask you to vote on a proposal to approve and adopt the Agreement and Plan of Merger, dated as of June 15, 2025, by and among Cantaloupe, 365 Retail Markets, LLC (which we refer to as “365”), Catalyst Holdco I, Inc. (which we refer to as “Holdco”), Catalyst Holdco II, Inc. (which we refer to as “Holdco II”) and Catalyst MergerSub Inc. (which we refer to as “Merger Subsidiary”), as it may be