FOURTH QUARTER 2023
EARNINGS PRESENTATION
February 15, 2024

FORWARD-LOOKING STATEMENTS
This presentation contains “forward-looking statements” within the meaning of the Private Securities Litigation Reform Act of 1995. These statements can be identified by the use of
forward-looking terminology such as “expects,” “believes,” “estimates,” “projects,” “intends,” “plans,” “goal,” “seeks,” “may,” “will,” “should,” or “anticipates” or the negative or othervariations of these or similar words, or by discussions of future events, strategies or risks and uncertainties. Specifically, forward-looking statements include, but are not limited to,statements regarding: future revenue and Adjusted EBITDAR; the Company’s expectations of future results of operations and financial conditions; the assumptions provided regarding
guidance, including the scale and timing of the Company’s product and technology investments; the Company’s expectations regarding results, and the impact of competition inretail/mobile/online sportsbooks, iCasino, social gaming, and retail operations; the Company’s development and launch of its Interactive segment’s products in new jurisdictions andenhancements to existing Interactive segment products, including the content for ESPN BET and theScore Bet; the benefits of the Sportsbook Agreement between the Company andESPN; the Company’s expectations regarding its Sportsbook Agreement with ESPN and the future success of its products; the Company’s expectations with respect to the integrationand synergies related to the Company’s integration of theScore and the continued growth and monetization of the Company’s media business; the Company’s expectations with respect
to the ongoing introduction and potential benefits of the cashless, cardless and contactless (3C’s) technology; the Company’s development projects, including the prospective
development projects; our ability to obtain financing for our development projects on attractive terms; the timing, cost and expected impact of planned capital expenditures on theCompany’s results of operations; and the actions of regulatory, legislative, executive or judicial decisions at the federal, state, provincial or local level with regard to our business and theimpact of any such actions.
Such statements are all subject to risks, uncertainties and changes in circumstances that could significantly affect the Company’s future financial results and business. Accordingly, theCompany cautions that the forward-looking statements contained herein are qualified by important factors that could cause actual results to differ materially from those reflected by suchstatements. Such factors include: the effects of economic and market conditions that could reduce discretionary spending; our ability to effectively compete in the global entertainment,sports content and casino gaming industries, our ability to successfully acquire and integrate new properties and operations; our ability to maintain our gaming licenses and concessions
and comply with applicable gaming law; win rates; changes in laws, including increased tax rates, regulations or accounting standards, third-party relations and approvals; risks
associated with the collection and retention of data about our customers, employees, suppliers and business partners; and additional risks and uncertainties described in the Company’s
Annual Report on Form 10-K for the year ended December 31, 2022, subsequent Quarterly Reports on Form 10-Q and Current Reports on Form 8-K, each as filed with the U.S.
Securities and Exchange Commission. The Company does not intend to update publicly any forward-looking statements except as required by law. Considering these risks, uncertainties
and assumptions, the forward-looking events discussed in this presentation may not occur.

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RECENT COMPANY HIGHLIGHTS
Generated >$2b in Property-Level EBITDAR in FY23 from our portfolioof 43 properties across the U.S.

Broke ground on our four retail growth projects in Illinois, Ohioand Nevada, all of which we expect to complete by 1H26

Launched ESPN BET on November 14, 2023 simultaneously in 17U.S. states, driving 1M+ new customers into our digital databaseAchieved record company U.S. OSB Handle in ESPN BET’s first
two full months of operations in Dec ’23 & Jan ’24 (+190% Y/Y) (1)Secured market access in two new OSB jurisdictions (NY & NC), both ofwhich we expect to launch in 2024
(1) Both Dec ’23 and Jan ’24 each represented record months of U.S. OSB Handle for the company. Y/Y refers to Y/Y growth in the period 12/1/23 – 1/31/24.

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RETAIL CORE DRIVES OMNI-CHANNEL STRATEGY
Our retail business remained healthy in FY23 and provides a foundation for our growth
initiatives as we continue to execute on our long-term omni-channel strategy$5.7b

43 Properties in 20 U.S. States

Retail Revenue(+8% vs. FY19)

29m+

$2b+

PENN PlayLoyalty
Database

Property-Level
EBITDAR(+20% vs. FY19)

35.8%
Property-Level
Margin(+361bps vs. FY19)v

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LAUNCH SUMMARYINITIAL DEMAND FAR EXCEEDS OUR EXPECTATIONS
Bolstered by the strongest brand in sports media, the launch of ESPN BET resulted in a muchhigher than expected wave of registrations, expanding our digital database by over 50%
The launch of ESPN BET drove more FTDs in
two months than we expected in the first year

Average Monthly Active Users (2)1M+New Registrations (1)from ESPN BET~1/3 of these new customers are located within 50
miles of one or more of our 43 retail properties

in 000s771
11/14
Launch251

272

Q4 '22

Q1 '23

196

189

Q2 '23Q3 '23Q4 '23+207% Growth Y/Y in Average MAUs in Q4 ‘23v

(1) Registrations, during the period of 11/14/23 – 12/31/23, defined as registrations by new customers who were not previously in our digital database. (2) Quarterly Average Monthly Active Users refers to our Average MAUs across OSB &iCasino globally in the period. MAUs are defined as the number of unique paid users per month that had at least one real money paid engagement across our Online Sports Betting and Online Casino products globally.

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ENCOURAGING RETENTION WITH DISCIPLINE
Strong retention and consistent user acquisition have led to steady M/M increases in Cash
Handle as our promotional expenses have started to normalize entering 2024
U.S. OSB MoM Trends
HandleJan ‘24
Cash Handle

Cash Handle+289%vs. pre-launchlevels (Oct ’23)

11/14
LaunchPromo Expense
as a % of Handle:

Sept '23

Oct '23

Nov '23

Dec '23

Jan '24

3.2%

2.0%

32.2%

10.7%

2.8%

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RETAINING STRONG BASE OF ACTIVE USERS
Based on Sensor Tower data, we have consistently held the #3 ranking in Weekly Active Users vs.
our top peers, providing a foundation for market share gains as we grow our monetization per user
% Share of Weekly Active Users (1)Total Time Spent on App(Sensor Tower Data)(Sensor Tower Data)

11%

10%

11%

10%

10%

12%

11%

11%

10%

11%

11%

11%

11%

12%

12%

11%

11%

11%

12%

11%

15%

16%

16%

16%

16%

15%

14%

15%

16%

15%

21%

21%

20%

22%

22%

22%

23%

22%

21%

21%

24%

24%

23%

24%

22%

23%

24%

24%

23%

22%

Week
Beginning

Nov '23

Competitor A

Competitor B

ESPN BET

Competitor C (DFS)

Competitor D

Competitor E (DFS)

Competitor F

Competitor G

Dec '23

Jan '23v(1) The Sensor Tower data shown is across the top available unified sportsbook & daily fantasy competitor apps including our top four market share competitors in OSB and two of the largest Daily Fantasy Sports apps. Sensor Tower defines
Weekly Active User as a user that has one or more sessions within a week. Data is subject to change per Sensor Tower policies.

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REACHING A WIDE RANGE OF SPORTS FANSESPN BET has helped us reach new demographics of sports fans that we view as incremental
to our database, resulting in increased parlay mix and a higher mix of non-NFL volumes Y/Y+63%
Y/Y Growth inParlay Mix (1)(of Handle)+360%
Y/Y Growth in(1)
Parlay Handle+40%
Y/Y Growth in
NBA Mix(1)(of Handle)(1) Y/Y metrics refer to growth in the period of 11/14/23 – 1/31/24. (2) Refers to Y/Y growth in Female % Mix of our total digital database as of 12/31/23.

+35%

Higher Mix of Females
Y/Y in our Digital
Database (2)v

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POTENTIAL TO GROW THE MARKETThe launch of ESPN BET in partnership with the strongest brand in sports media highlights
the potential to broaden the appeal of sports betting and grow the overall market

Nov-Dec Market Handle ($b) (1)Market Analysis of U.S.
States with publicly
available data for both
November and December
2023 that were live in
November 2022

BeforeESPN BET+17%
Y/Y Growth

Nov-Dec ‘23
Market Handle

States Included: NJ, PA,MI, MD, TN, WV, LA, IA,IN, KS, CO, IL & VA

After
ESPN BET
2022

Total Market(1) Sources: State Gaming Reports and PENN internal data.

Jan-Oct ‘23
Market Handle

ESPN BET launched in Nov ‘232023

Market Ex-PENN+29%
Y/Y Growth+25%
Y/Y Growth
Ex-PENNv

10POSITIVE IMPACT ON HOLLYWOOD iCASINO
The successful launch of ESPN BET has bolstered our Hollywood-branded iCasino business,
which has seen a significant increase in active users, providing a platform for future growth
Average U.S. iCasino MAUs

New Proprietary Content
from Penn Game Studios

Q4Releases+280%

11/14Launch

Y/Y Growth

Jan ‘24
Releases

Q4 '22

Q1 '23Q2 '23Q3 '23Q4 '23v(1) Quarterly Average U.S. iCasino MAUs refers to our Average Monthly Active Users for our U.S. iCasino product offering. MAUs are defined as the number of unique paid users per month that had at least one real money paid engagementon our U.S. iCasino product offering.

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PRODUCT, INTEGRATION, &MARKETING HIGHLIGHTSESPN.com Homepage

INITIAL BET MODE INTEGRATION IN THE ESPN APP
January 11, 2024
6-Pack Integration•ESPN has enabled “Bet Mode” onits ESPN media app & website,
providing users with an enhanced
media and betting experience•Our ESPN BET 6-pack odds
integration into the ESPN MediaApp provides a seamless clickthrough from ESPN Gamecast todesired bet(s) page in ESPN BET•These integrations allow ESPN BETto acquire and engage with users
directly through the ESPN App(28m MAUs)v

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BRAND & MARKETING HIGHLIGHTS
Our comprehensive strategic alliance with ESPN is providing exceptional marketing value as
we integrate directly with ESPN’s top shows and talentHigh-Value Segments & Integrations in ESPN’s Top Studio Shows

Unique Activations
Erin Dolan & Elle Duncan hosting our VIP Big
Game Party at M Resort in Las Vegasv

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BRAND & MARKETING HIGHLIGHTS (CONT’D)
Collaboration with ESPN’s best-in-class teams on ESPN BET’s branding and campaign
strategy is driving high-quality, branded marketing content
Talent-led Brand Campaigns
Elle Duncan“You Had To Be There”

Mike Greenberg“The Elements”

Kendrick Perkins“Big Man”

Erin Dolan“Erin Dolan Talks ESPN BET”

ESPN.com & ESPN App Takeovers

Industry-leading Social Media

10m+Account Followers (1)(1) Total ESPN BET Social Media Account Followers across X, Instagram, Facebook, & TikTok.

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BRAND & MARKETING HIGHLIGHTS (CONT’D)
Multi-faceted marketing strategy with ESPN, leveraging key talent and our respective
databases, is leading to attractive customer acquisition costs and efficiencies$150m in Annual Payments to ESPN includes:*•Brand License*•Traditional Advertising•Linear Media Integrations*•Digital Media Integrations*•CRM, including access to ESPN’s leading fantasy
database*•Collaboration with ESPN’s best-in-class Product,Technology, Marketing, & Creative teams*•Access to ESPN Events & Talent*

Denotes exclusive ESPN licenses, integrations, and promotional services, in Sports
Betting, iGaming, DFS, and Horse Race Wagering, subject to certain limited exceptions

Disciplined Marketing Efficiency
We will achieve greater marketing efficiency from our nationalreach with ESPN as we increase scale from new states$150m Annual ESPN Spend (Per Capita)

20%Reduction in percapita spend
with addition ofNC & NY

Current 17 U.S. States(+) NC & NYv

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ADDITIONAL GROWTH OPPORTUNITIES IN 2024
New York (1)1st ESPN BET Retail Sportsbook(+) Pending acquisition of OSB access in the state of NY
with an expected launch before the 2024 NFL season
6% of the U.S. Population(+) Inaugural ESPN BET-branded Retail Sportsbook set
to open in Detroit, MI in 2Q24 at Hollywood Casino atGreektown

North Carolina(+) Grand Opening to coincide with the NFL Draft in April,creating a unique omni-channel experience withESPN Events and Talent for VIPs, Clients, & Fans

(1)(+) Launch of OSB in North Carolina is expected on
March 11th, 2024
3% of the U.S. Population

AfterToday

37%of theU.S.
Population(1) Pending regulatory approvals.

Hollywood at Greektown rendering+25% increase

46%of theU.S.
Populationv

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