FIRST QUARTER 2024
EARNINGS PRESENTATION
May 2, 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 condition; the assumptions provided regarding theguidance, including the scale and timing of the Company’s product and technology investments; the Company’s expectations regarding results and customer growth, retention andspend; the impact of competition, in retail/mobile/online sportsbooks, iCasino, social gaming, and retail operations; the Company’s development and launch of its Interactive segment’sproducts in new jurisdictions and enhancements to existing Interactive segment products, including products and content for ESPN BET and theScore Bet; the benefits of the Sportsbook
Agreement between the Company and ESPN; the Company’s expectations regarding its Sportsbook Agreement with ESPN and the future success of ESPN BET; the Company’sexpectations with respect to the integration and 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 that its portfolio of assets provides a benefit of geographically-diversified cash flows from operations; the Company’s plan to expand gaming
operations through the implementation and execution of a disciplined capital expenditure program at our existing properties, the pursuit of strategic acquisitions and investments, and thedevelopment of new gaming properties, including the prospective development projects; improvements, expansions, or relocations of our existing properties; entrance into newjurisdictions; expansion of gaming in existing jurisdictions; strategic investments and acquisitions; cross-sell opportunities between our retail gaming, online sports betting, and iCasino
businesses; our ability to obtain financing for our development projects on attractive terms; the timing, cost and expected impact of planned capital expenditures on the Company’sresults 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 the impact ofany 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 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 gaming industries; our ability to achieve the anticipated financial returns from the Sportsbook Agreement with ESPN, including due to fees, costs, taxes or
circumstances beyond the Company’s or ESPN’s control; the timing, cost and expected impact of product and technology investments; the ability of the Company or ESPN to retain andhire key personnel; our ability to successfully acquire and integrate new properties and operations; our ability to maintain our gaming licenses and concessions and comply withapplicable gaming law; win and hold rates; changes in laws, including increased tax rates, regulations, or accounting standards; third-party relations and approvals; risks associated withthe collection and retention of data about our customers, employees, suppliers and business partners, and additional risks and uncertainties described in the Company’s Annual Reporton Form 10-K for the year ended December 31, 2023, subsequent Quarterly Reports on Form 10-Q and Current Reports on Form 8-K, each as filed with the U.S. Securities andExchange Commission. The Company does not intend to update publicly any forward-looking statements except as required by law. Considering these risks, uncertainties andassumptions, the forward-looking events discussed in this presentation may not occur.

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RECENT COMPANY HIGHLIGHTS
Resilient property-level performance, with stable trends continuing intoApril following portfolio-wide severe weather through mid-February

Achieved record OSB handle and iCasino GGR, while OSB results
were impacted by lower than expected hold and spend per user

PENN Play Database grew to 30 million, including 3.6 million inour digital database (+71% since ESPN BET Launch)

Launched ESPN BET in North Carolina on March 11th, bringing ourOSB footprint to 18 U.S. States and Ontario

Announced the hiring Aaron LaBerge as Chief Technology Officer, who
joins the company from Disney & ESPNv

3HEALTHY RETAIL BUSINESS
Weather events in January and early February impacted all of our regional property segments;
however, both visitation and volumes subsequently recovered with stable trends continuing into April

We continue to capitalize on cross-sellopportunities from our retail sportsbooks,
which has helped sustain momentum in ourOhio properties and re-energize properties
such as Plainridge Park in MA and Hollywood
Casino at Kansas Speedway

Inaugural ESPN BET
Retail Sportsbook inMI opened in Aprilv

4

SEQUENTIAL M/M IMPROVEMENTS IN RETAIL
Several properties achieved record EBITDAR in the February-March period as both volumes andEBITDAR margins rebounded following the severe weather impacts
Q1 Property Highlights:

Q1 Retail Performance
Revenues

EBITDAR

EBITDAR Margins$ 60 0 .0

4 5.0 %

• 8 properties achieved record combined
EBITDAR across February – March

4 0. %$ 50 0 .0

3 5.0 %

$ 40 0 .0

3 0. %• We experienced particular strength inOhio, Massachusetts, Maryland and ournew properties in Pennsylvania

2 5.0 %

$ 30 0 .0

2 0. %$ 20 0 .0

1 5.0 %

1 0. %$ 10 0 .05 .0%$ -0 .0%JanuaryFebruaryMarchv

5

ESPN BET’S FIRST RETAIL SPORTSBOOK - DETROIT
We opened our first ESPN BET retail sportsbook on April 25th in connection with ESPN’s live coverage ofthe NFL draft at Hollywood Casino at Greektown, showcasing the property and brand to new customers

Hollywood Casino at
Greektown in Detroit, Michiganv

6

ESPN MARKETING HIGHLIGHTS
We have continued to expand the depth and impact of our content integrations with ESPN throughout
the year as we now enter basketball and hockey playoffs, and the beginning of baseball seasonv

7INTERACTIVE TOP-OF-FUNNEL SUCCESS CONTINUESESPN BET has driven meaningful growth in both our digital database and active user base,providing a strong foundation for future growth
Total Digital Database (M)
3.6

771

3.2

685in 000s

11/14/23
LaunchAverage Monthly Active Users (1)

2.1
1.7

272

0.9

2021

2022+71%

Q3 '23Q4 '23

Q1 '24Growth in Digital Databasesince our ESPN BET Launch

Q1 '23

196

189

Q2 '23Q3 '23+152%

Q4 '23

Q1 '24

Y/Y Growth in MAUs in
Q1 ’24 vs. Q1 ‘23v

(1) 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.

8

RETAINING STRONG BASE OF ACTIVE USERS
Based on Sensor Tower data, we continue to hold the #3 ranking in Weekly Active Users
among our top OSB and DFS competitors% Share of Weekly Active Users (1)Total Time Spent on App

Sensor Tower Data

12%

11%

11%

11%

17%18%

16%

18%

17%

18%

17%

17%

17%

17%

19%

18%

20%

20%

21%

21%

20%

22%

21%

20%

21%

21%

21%

20%

22%

21%

21%

21%

21%

21%

4

12%

412%

4/
22/2
02

12%

4/
15/2
02

12%

4/
8/
20
24

10%

4/
1/
20
24

11%

4

10%

3/
25/2
02

10%

4

10%

4

9%

3/
18/2
02

9%

3/
11/2
02

9%

3/
4/
20
24

10%

4

10%

412%

2/
26/2
02

12%

2/
19/2
02

Week
Beginning(Sensor Tower Data)

Competitor A

Competitor B

ESPN BET

Competitor C (DFS) Competitor D

Competitor E (DFS)

Competitor F

Competitor G

Competitor H

Jan '24

Feb '24

Mar '24v(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.

9INTERACTIVE REVENUE IS TRENDING POSITIVELYInteractive Revenue showed strong Q/Q growth, as promo expenses began to normalize after the
initial ESPN BET launch despite a new state launch in North Carolina
Promo Expense as a % of Handle
U.S. OSB

Interactive Revenue ($M)

Total Online (OSB & iCasino)

Revenue

Revenue (excl. tax gross up) (1)$207.7
11/14/23
Launch

16.7%

+559%
Q/Q Growth

$91.1

$31.5
7.8%
4.8%
2.5%

2.6%

1.2%
Q1 '23Q2 '23Q3 '23Q4 '23

Q1 '24($75.5)Q4 '23

Q1 '24v(1) Tax gross-up refers to the gaming taxes which PENN Interactive pays on behalf of, and is reimbursed by, its third-party online sports betting and iCasino operator partners that PENN provides market access to in various states in the U.S.

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OSB: RECORD HANDLE IN Q1We achieved record OSB Handle in Q1 ‘24 and strong Y/Y growth in GGR despite the negative
impact of unfavorable hold for major sporting events in the quarter
OSB Handle

OSB GGR

11/14/23
LaunchQ1 '23Q2 '23+96%

Q3 '23Q4 '23

Q1 '24

Y/Y Growth in OSB Handle inQ1 ‘24 vs. Q1 ‘23

Q1 '23Q2 '23+51%

Q3 '23Q4 '23

Q1 '24

Y/Y Growth in OSB GGR in
Q1 ‘24 vs. Q1 ‘23v

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OSB: U.S. HOLD ANALYSIS
While unfavorable hold impacted us in the quarter, we have seen an improvement to start Q2 andare focused on closing the current gap in hold vs. our top 2 competitors
Q1 ’24 OSB % Hold
(IA, IN, KS, MA, MD, MI, PA)

ESPN BET % Hold(1)

(Total U.S.)
~8.5%

4.4%

Competitor A

Competitor B

Rest of Market

ESPN BET

Q1 '24(1) Eilers & Krejcik Reports and Public State Gaming Reports – the chart utilizes state data from states that report handle and GGR by operator with available data through March 2024.

Apr '24v

12OSB: U.S. HOLD ANALYSIS (CONT’D)
Our hold underperformance v. our top 2 competitors is driven primarily by a lower mix of parlays,
which we plan to address with our updated product offering this Fall
Illinois OSB: Parlays as a % of Total Handle(Jan '24 - Feb '24)

Illinois OSB: Parlays as a % of Total Bets
(Jan '24 - Feb '24)
65%

36%

56%

26%
22%

Competitor A

Competitor B

ESPN BET

21%

Rest of Market

Competitor ACompetitor B

Note: Illinois uniquely reports U.S. OSB data by operator at a granular level thatincludes bet types. March IL OSB data is not yet available.
Source: Eilers & Krejcik Reports and Public State Gaming Reports.

44%

41%

ESPN BET

Rest of Marketv

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OSB: AVG. SPEND PER USER
Despite a dramatic Y/Y increase in MAUs, our spend per user has been lower than expected, which
we believe is due primarily to lower share of wallet from identified gaps in product
MAU & Average Handle Per MAU (U.S. OSB) (1)Monthly Active Users

Average Handle Per MAU

8 0 ,0 0$ 1,8 0 0$ 1,6 0 0
7 0 ,0 0$ 1,4 0 0

6 0 ,0 0$ 1,2 0 0

5 0 ,0 0$ 1,0 0 0

4 0 ,0 0$ 80 0

3 0 ,0 0$ 60 0

2 0 ,0 0$ 40 0

1 0 ,0 0$ 20 0-$ 0

Q1 '23(1) Excludes VVIP Play.

Q2 '23Q3 '23Q4 '23

Q1 '24v

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iCASINO: RECORD GGR IN Q1
Improved cross-sell from ESPN BET to Hollywood Casino led to record iCasino Handle and GGR inQ1, and we expect our standalone Hollywood iCasino app to be highly incremental once live(1)iCasino MAUsiCasino GGR

11/14/23Launch

Q1 '23Q2 '23+166%

Q3 '23Q4 '23

Q1 '24

Y/Y Growth in iCasino MAUs in
Q1 ’24 vs. Q1 ‘23(1) We expect to launch our standalone Hollywood iCasino app in late 2024 or early 2025.

Q1 '23Q2 '23+32%

Q3 '23Q4 '23

Q1 '24

Y/Y Growth in iCasino GGR in
Q1 ’24 vs. Q1 ‘23v

15

PRODUCT UPDATES: Q1 HIGHLIGHTSSmooth performance during the Big Game on our proprietary
player account management and risk & trading platform

My Bets page redesign, including Live Stat Tracking
Released parlay repricing functionality to account forparlay bet legs that push or void
Made enhancements to instant payments and our player
identification processes
Launched 3 new iCasino games developed by Penn Game
Studios, including our new Toronto Blue Jays Blackjack

My Bets page redesign
with Live Stat Trackingv

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WORLD-CLASS TECHNOLOGY LEADERSHIP
We have been thrilled with the top of funnel effectiveness of our partnership with ESPN and are hyperfocused on improving our digital offerings in 2024 and beyond to capitalize on our expanded user base
New Role – Chief Technology Officer• On April 22, 2024, we announced the hiring of Aaron LaBerge as our Chief
Technology Officer• Mr. LaBerge will be responsible for driving technology strategy and execution forPENN, while leading the multinational team of technologists and serving as thekey business leader for the company’s Interactive division
Impressive Track Record• Mr. LaBerge spent more than 20 years at The Walt Disney Company – mostrecently as President & Chief Technology Officer for Disney Entertainment andESPN, where he was responsible for driving all technology and productdevelopment in support of The Walt Disney Company’s two media divisions
Aaron’s prior experience as President &CTO of Disney Entertainment and ESPN will
be invaluable as we execute on our
technology-forward, omni-channel strategy• In that role, he helped set the vision and strategic leadership for how Disney uses
technology to enable storytelling and innovation, drive its business, and create
unparalleled consumer experiences with entertainment and sports content
17v

ESPN BET PRODUCT ROADMAP

Upcoming Football Season (1)Our upcoming ESPN BET product roadmap priorities will bring us closer to product parity with key
competitors this football season and help activate our fast-growing database

Refreshed User Interface & Experience• Home Page Improvements• Parlay Carousel Functionality• Dark Mode
• Dedicated “Parlay Lounge”

New Features & Functionalities• Improved Profit Boost Offerings• Expanded Same Game Parlay Breadth• Referral Program(+) ESPN BET Integration into
• Early Win Payouts
theScore Media App in the U.S.
v(1) The items on our product roadmap slides are items we expect to unveil during this upcoming football season, the majority of which we expect to be ready by the start of the NFL season.

18ESPN BET PRODUCT ROADMAP

Upcoming Football Season (1)We are already seeing the benefits of our digital integrations
with ESPN, with a strong roadmap ahead

300K

Expansion of Deep-Linked Odds within ESPN Digital Products

Scores Page•

Scores Page in ESPN App•

Home Page in ESPN App•

More Odds Markets (e.g., Prop Markets) and Dedicated “Odds” and“Futures” Pages in ESPN App•

ESPN Fantasy App (FantasyCast & Personalized Offers) – see slide 20Unique Visitors to ESPN BET fromlinks in ESPN’s Digital Products
during the month of MarchHome Page

ESPN Watch Options & Gamecast Linkouts within ESPN BET•

Direct links in ESPN BET to (1) Watch Options like ESPN & ESPN+Streams and (2) Gamecast in the ESPN App

Account Linking (ESPN <> ESPN BET)
•Linking user accounts will unlock cross-product personalization•This also unlocks future features like Bet Tracking & Embedded Bet Slips(1) The items on our product roadmap slides are items we expect to unveil during this upcoming football season, the majority of which we expect to be ready by the start of the NFL season.

v

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ESPN BET PRODUCT ROADMAP

Upcoming Football Season (1)Integration into the #1 Fantasy Sports App
ESPN BET will be integrated into the category leading
ESPN Fantasy App by football season, including deeplinked markets and personalized in-app betting offers

#1

Fall
2024

Fall
2024

Ranked Fantasy
Sports App in the U.S.

12M Fantasy Football Players

By the end of the year, we plan to implement
Account Linking capabilities to provide personalizedexperiences inside ESPN BET based on a user’s
ESPN Fantasy Team and ESPN Favorites
Personalized Offers in
ESPN Fantasy(1) The items on our product roadmap slides are items we expect to unveil during this upcoming football season, the majority of which we expect to be ready by the start of the NFL season.

v

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APPENDICESOMNI-CHANNEL STRATEGY

Retail Gaming

Media & Content

Online Gaming

43 Properties in 20 U.S. States

Strategic Sports Betting Alliance with ESPN

Online Sportsbook Live in 18 U.S. States + Ontario

32 Retail Sportsbooks in 15 U.S. States

theScore Media App (Wholly-Owned)

Online Casino Live in 4 U.S. States + Ontario

30M+LOYALTY PROGRAM
MEMBERS(1) We have added >3m new members over the last 2 quarters, highlighting the power of ESPN BET and our continued success in acquiring members at retail.

(1)v

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