PENN Entertainment, Inc.

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

(Amendment No. )

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Filed by a Party other than the Registrant ☐

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A LETTER TO OUR SHAREHOLDERS

Dear Fellow Shareholders,

Over the past year, we have made meaningful changes at PENN and believe our investments in technology, combined with our retail growth projects, position us well for 2026 and beyond. We have advanced our core retail business, strengthened Board oversight, refined our operating structure and repositioned our digital strategy – all with a focus on delivering sustainable, long-term value.

As we look ahead, our priorities are clear: execute with discipline, drive profitable growth, increase free cash flow and enhance shareholder returns.

Stronger Governance for Our Next Phase of Growth and Execution

We are committed to strong governance practices, including with respect to the evolution of our Board’s skillsets. Board refreshment at PENN is thoughtful and deliberate to ensure we have the right expertise and perspectives present in the Boardroom to oversee our strategy. In the past 12 months, we have appointed five new independent directors, meaningfully strengthening the Board’s composition, independence and competencies.

In 2025, we appointed independent directors Carlos Ruisanchez and Johnny Hartnett to the Board, and earlier this year we added three additional highly qualified independent directors – Heather Ace, Jeffrey Fox and Fabio Schiavolin. Our refreshed Board’s expanded expertise in global gaming, digital operations, human capital, finance and technology positions us to guide PENN through the disciplined execution of its next phase of growth.

Refocused Digital Strategy

In late 2025, following the mutual early termination of our exclusive U.S. online sports betting agreement with ESPN, we repositioned our digital strategy around a more focused and efficient model centered on iCasino growth, cross-sell and omnichannel engagement. This shift allows us to enhance integration across our ecosystem and better leverage our retail footprint in the U.S. and strength in Canada.

Our approach to digital is no longer driven by scale alone; it is grounded in durable economics, disciplined investment and long-term returns. PENN’s retail footprint, media assets and technology capabilities provide a differentiated platform for integrating retail and digital engagement. The omnichannel ecosystem we built allows us to strengthen customer relationships, enhance marketing precision and drive greater value across both physical and online platforms.

We are focused on expanding cross-channel engagement, leveraging data and analytics to optimize promotional effectiveness, strengthening the loyalty ecosystem and improving the return profile of customer acquisition investments. This integrated, disciplined approach is designed to support more sustainable growth and long-term value creation.

Simplified Organizational Structure Advances Strategic Priorities

In January 2026, PENN implemented a new corporate organizational structure designed to align our operations with our strategic priorities, including a more focused approach to our digital business and deeper integration with our core retail and omnichannel model. This realignment centralized key technology, data and digital capabilities under unified leadership, simplified reporting lines and reduced duplication across the organization. We expect these changes to improve operating efficiency, support stronger cross-channel engagement and contribute to increased free cash flow over time.

These changes are projected to generate over $10 million in annualized run-rate cost savings, the majority of which will be realized in the first half of 2026.

Disciplined Capital Allocation

Disciplined capital allocation remains central to our strategy. We deploy capital through a balanced framework: investing in high-return retail development and property enhancements, leveraging our prior investments in Interactive initiatives, reducing leverage and repurchasing shares opportunistically.

A LETTER TO OUR SHAREHOLDERS

In 2025, we repurchased $354 million of shares, bringing total repurchases since 2022 to $1.1 billion, or approximately 25% of shares outstanding. These actions underscore our commitment to returning capital to shareholders while maintaining financial flexibility.

We expect meaningful free cash flow generation in 2026, providing capacity to further reduce leverage, invest in high return projects and continue evaluating share repurchases as conditions warrant.

Looking Ahead

With a strengthened, refreshed Board, a more efficient organization and a disciplined digital strategy, we are confident in our ability to drive long-term growth and create value for shareholders.

We believe the actions we took in 2025 enhanced our operational and financial foundation, positioning PENN for continued performance improvement in 2026 and beyond. We remain focused on driving continued growth across our retail portfolio, achieving break-even adjusted EBITDA in Interactive 1, maintaining disciplined capital allocation and financial flexibility while further deleveraging, and realizing the benefits of our recent organizational enhancements.

PENN’s success is driven by the dedication of our more than 23,000 team members and our commitment to being a responsible partner in the communities we serve. We are proud of the continued progress our Company has made in advancing our corporate responsibility priorities and remain focused on building on this momentum in the years ahead.

On behalf of our Board and leadership team, we would like to thank you, our valued shareholders, for your continued investment, support and confidence. 2026 is sure to be an exciting year at PENN Entertainment.

NOTICE OF ANNUAL MEETING OF SHAREHOLDERS

This summary highlights information contained elsewhere in this Proxy Statement. This summary does not contain all of the information you should consider, and you should read the entire Proxy Statement before voting.

Items of Business

At or before the PENN Entertainment, Inc. 2026 Annual Meeting of Shareholders (“Annual Meeting”), shareholders will vote on the following items:

Proposal 1: Election of Class III Directors

Proposal 2: Ratification of Appointment of Independent Registered Public Accounting Firm

Proposal 3: Advisory Vote to Approve the Compensation of Named Executive Officers

Proposal 4: Approval of the Third Amendment to our 2022 Long-Term Incentive Compensation Plan

Proposal 5: Advisory Vote on a Shareholder Proposal Requesting Annual Election of Directors, if properly presented

Shareholders will also transact such other business as may properly come before the Annual Meeting and any postponement or adjournment thereof.

Voting

Each share of common stock held by a shareholder of record of such common stock as of the close of business on March 27, 2026 is entitled to vote on each of the items to be voted on at the Annual Meeting.

Your Vote is Very Important

Your vote is extremely important no matter how many shares you own. Whether or not you expect to attend the Annual Meeting, please promptly use your proxy card to vote by proxy over the internet or by mail. If you have any questions or require any assistance with voting your shares, please call PENN Entertainment’s proxy solicitor:

INNISFREE M&A INCORPORATED

Shareholders may call 1 (877) 800 - 5187 (toll-free from the U.S. and Canada) or

+1 (412) 232-3651 (from other countries)

Banks and Brokers may call collect 1 (212) 750-5833

DATE AND TIME June 16, 2026 at 10 a.m. ET

VIRTUAL MEETING:The Annual Meeting is a virtual meeting atwww.virtualshareholdermeeting.com/PENN2026

RECORD DATE: March 27, 2026 Only shareholders of record as of the close of business on the Record Date will be entitled to notice of and to vote at the Annual Meeting.

ATTENDANCE:Only shareholders of record or their legal proxies may participate in the virtual Annual Meeting.

NOTICE OF ANNUAL MEETING OF SHAREHOLDERS

Proxy Voting Methods

Even if you plan to attend the virtual Annual Meeting, please vote right away by using one of the following advance voting methods. Make sure to have the proxy card or voting instruction form in hand and follow the instructions. You can vote in advance in one of four ways:

Your vote is important. We encourage you to vote promptly, regardless of whether you plan to attend the Annual Meeting.

By Order of the Board of Directors,

Christopher Rogers

Executive Vice President, Chief Strategy and Legal Officer and Secretary

Wyomissing, Pennsylvania

April 27, 2026

IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE ANNUAL MEETING TO BE HELD ON JUNE 16, 2026: Our Proxy Statement and the 2025 Annual Report are available free of charge on our website at https://investors.pennentertainment.com/reports-filings/sec-filings. In addition, our shareholders may access this information, as well as submit their voting instructions, at www.proxyvote.com.

NOTICE OF ANNUAL MEETING OF SHAREHOLDERS

Attendance at Meeting

To attend the virtual Annual Meeting, you must be a shareholder on the Record Date and have previously registered to attend the meeting. Register to attend the Annual Meeting on or before 9:45 a.m. ET on June 16, 2026 by visiting www.proxyvote.com. You will need the 16-digit control number found on your proxy card or voting instruction form. You will receive a confirmation e-mail with information on how to attend the meeting. After you have registered, you will be able to participate in the Annual Meeting by visiting www.virtualshareholdermeeting.com/PENN2026 and entering the same 16-digit control number you used to preregister and as shown in your confirmation e-mail.

Beneficial shareholders who do not have a 16-digit control number should follow the instructions provided on the voting instruction form provided by your broker, bank, or other nominee. In addition to registering for the meeting, beneficial holders that wish to vote at the meeting must obtain a legal proxy from their bank, broker, or other nominee prior to the meeting. You will need to have an electronic image (such as a pdf file or scan) of the legal proxy with you if you are voting at the meeting.

Electronic entry to the virtual Annual Meeting will begin at 9:45 a.m. ET, and the Annual Meeting will begin promptly at

10:00 a.m. ET. If you encounter difficulties accessing the virtual Annual Meeting, please call the technical support number that will be posted at www.virtualshareholdermeeting.com/PENN2026.

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