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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A LETTER TO OUR SHAREHOLDERS

Dear Fellow Shareholders,

PENN Entertainment is navigating a pivotal chapter—anchored by our legacy of operational excellence and guided by a clear, long-term vision. Over the past several years, we’ve made meaningful investments to modernize our business and build a foundation for sustainable growth and shareholder value creation. While the execution of our digital strategy has introduced near-term volatility in our operational performance, we are beginning to see indicators of progress that validate our strategy as we leverage our rapidly growing database. With the proliferation of both legalized online sports betting and online gaming continuing across North America, we view it as imperative to have an omnichannel relationship with our customers to successfully compete long term.

We recognize that recent shareholder returns have fallen short of expectations. Our Board and management team remain fully committed to returning to the level of performance and value creation that has been a hallmark of PENN over the past three decades.

Retail Leadership, Built to Last

PENN continues to set the standard for operational excellence and customer experience in regional gaming. We have the nation’s largest and most geographically diversified collection of regional assets in the industry, spanning over 40 properties across 20 states. Our retail business leads the industry in tax-adjusted margins and remains a model for operational consistency and efficiency. At the same time, we are consistently rated as one of the top employers of choice in gaming. While some companies lose focus in the pursuit of digital growth, we’ve held the line—maintaining and leveraging our core strength even as we expand our capabilities.

Today, our retail operations are thriving, gaining market share in key regions across the country, attracting a younger customer base, and tangibly benefitting from our digital investments through increased cross-channel engagement.

We are also advancing five exciting retail development projects—in Joliet, Las Vegas, Columbus, Aurora, and Council Bluffs—four of which are nearing completion over the next twelve months and continue to be on or ahead of schedule and on budget. These projects will further strengthen our competitive position and support long-term earnings growth.

Omnichannel Strategy: Early Results and Ongoing Execution

Our omnichannel strategy is central to our vision and long-term viability. The ability to engage customers across platforms—retail and digital—is already proving to be a differentiator in the gaming industry as it has across other categories of the consumer and retail sector.

We are seeing steady growth in our digital Monthly Active Users, with a significant portion of these customers located near PENN properties. This geographic overlap reinforces the value of our omnichannel ecosystem—where data, loyalty, and best-in-class experiences come together to drive digital engagement and incremental retail visitation and revenues.

We have also seen a meaningful shift in our customer demographics. Our average active PennPlay loyalty program member is now in their mid-40s, nearly a decade younger than in 2020, driven in large part by the reach of our digital channels, combined with the strategic capital investments we’ve made to appeal to a younger demographic.

Most importantly, we’re seeing that customers who interact with us across both channels are significantly more valuable than those who interact with us in digital or retail alone. For example, retail customers in Pennsylvania and Michigan who engaged with our new Hollywood iCasino app in Q1 2025 combined to generate over 25% year-over-year increases in retail theoretical revenue and over 190% year-over-year increases in online theoretical revenue for the same period. In addition, over 40% of our standalone iCasino users to date are new to our digital ecosystem, many of whom were retail customers previously playing online with our digital-first competitors. We remain convinced that establishing and maintaining a digital relationship with our customers is essential, and that offering a unified experience across our various platforms will increase play and generate greater loyalty and enhanced value per customer. This value creation opportunity is significant, and the Board and management team are closely monitoring our progress while remaining disciplined in our allocation of capital.

A LETTER TO OUR SHAREHOLDERS

Technology Leadership

We have made several strategic investments over the last five years to build out a robust digital platform and assemble a world-class team to lead our digital evolution, headed by Aaron LaBerge, former Chief Technology Officer of The Walt Disney Company. Under Aaron’s leadership, we’ve added high-impact talent across product, design, engineering, marketing and analytics, and we are now executing with greater speed and precision.

Our digital offerings are powered by a cutting-edge, fully-owned technology stack. We believe that ownership of our technology is critical to long-term success, providing not just material cost savings, but also greater control of our technological roadmap and the ability to accelerate new features and products. Our new standalone Hollywood iCasino app, for instance, is gaining share and starting to contribute meaningfully to gross margin. Our app was recently ranked the #2 iCasino product in the U.S. by Eilers & Krejcik—validation of the work our talented team is doing to build a competitive digital experience.

Sports Betting: Focused on Long-Term Alignment

Our sports betting strategy, including our partnership with ESPN, remains a key area of focus. Sports betting is the primary driver of customer acquisition for our entire omnichannel ecosystem. ESPN is a globally respected sports brand, and the integration of their media platform with our betting product gives us a unique opportunity to engage fans and bettors.

That said, our market share and financial performance in sports betting to date has not met our expectations. Our Board and management team are moving swiftly and decisively to recalibrate execution and unlock the full value of this partnership. We have a committed partner and shared desire to compete and build share in a financially responsible way. While our initial integrations have expanded reach and driven customer acquisition, we recognize there’s more work to do to deliver on the full potential. As mentioned on our Q4 earnings call, we are optimistic that our joint efforts with ESPN will deliver improved results over the coming quarters, but we maintain optionality and control of our future in this vertical if this does not prove to be the case.

Execution, Disciplined Capital Allocation and Shareholder Value Remain Top Priorities

PENN ended 2024 with $1.7 billion in liquidity and a strengthened balance sheet. We’ve announced plans to repurchase at least $350 million of stock this year, reflecting our confidence in the long-term value of our assets and strategy.

Over the next twelve months, we expect to:

We are clear-eyed about where we stand. The significant digital investments have been made and are beginning to yield results. Our core business remains very strong. Our omnichannel platform is continuing to build and gain traction. Our focus now is on best-in-class operational execution, which will transform our strategic investments into consistent, long-term results and value creation for our shareholders.

We are confident that PENN’s best days are ahead—and we are moving with speed, discipline, and determination to realize the full potential of this company for our shareholders.

Thank you for your continued investment.

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. 2025 Annual Meeting of Shareholders (“Annual Meeting”), shareholders will vote on the following items:

Proposal 1: Election of Class II 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 Second Amendment to our 2022 Long-Term Incentive Compensation Plan

Proposal 5: Approval, on an advisory basis, of a shareholder proposal regarding the commissioning of a report on the effects of a company-wide non-smoking policy

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 April 28, 2025 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) 717-3898 (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 17, 2025 at 10 a.m. ET

VIRTUAL MEETING:The Annual Meeting is a virtual meeting atwww.virtualshareholdermeeting.com/PENN2025

RECORD DATE: April 28, 2025 Only shareholders of record as of the close of business on April 28, 2025, 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

The accompanying Proxy Statement is dated April 28, 2025 and is first being mailed to shareholders beginning on or about April 30, 2025.

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 17, 2025 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/PENN2025 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/PENN2025.

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