NASCAR Enjoy Illinois 300 Long Shot Predictions & Sleeper Picks: World Wide Technology Raceway

Robert Criscola - Betting Analyst at Covers.com
Robert Criscola • Betting Analyst 11+ years betting experience
Updated: Sep 11, 2026 , 12:36 PM ET • 4 min read

Robert Criscola's long-shot predictions and sleeper picks for the Enjoy Illinois 300 on Sunday, Sept. 13 include Ty Gibbs.

NASCAR Cup Series Ty Gibbs
Photo By - Reuters Connect. NASCAR Cup Series driver Ty Gibbs.

After a thrilling postseason opener, the NASCAR Cup Series odds look for an encore in the Enjoy Illinois 300 at World Wide Technology Raceway.

My Enjoy Illinois 300 long-shot predictions and sleeper picks believe Joey Logano is offering value.

Read more in my free picks for Sunday, Sept. 13.

NASCAR Enjoy Illinois 300 sleeper picks

Driver Name Kalshi
Joey Logano 9%
Ty Gibbs 8%
Josh Berry 4%

Picks made on 9-11. For help understanding Kalshi probabilities, see our odds calculator.

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NASCAR Enjoy Illinois 300 long-shot predictions

Sleeper pick to win: Joey Logano
Kalshi probability: 9%

Joey Logano won the first ever Cup Series race at World Wide Technology Raceway in 2022, and there's little evidence in three subsequent races to suggest that was a fluke effort.

Logano has finished no worse than fifth in four career starts here, picking up six total stage placings. He hasn't led a ton of laps at WWT Raceway (22 of his 25 laps led came in 2022), but his lowest average driver rating in four starts is 99.

The No. 22 driver is in good form overall with two wins from the last seven races, and two additional Top 10s.

Play to 12%.

Sleeper pick to win: Ty Gibbs
Kalshi probability: 8%

Ty Gibbs' prior form at Gateway isn't dazzling, but it isn't disqualifying either — his average finish from three starts is 13.67 with a Top 10, a stage placing, and one lap led.

However, given his massive jump in overall form in 2026, it's not outrageous to expect Gibbs to get the win on Sunday.

Gibbs picked up his first two Cup Series wins this season, one of which came at an Iowa course that requires heavy braking, just like WWT Raceway. He's also posted a career-high 11 Top 5s, including last week's runner-up effort in the Southern 500 at Darlington.

Play to 10%.

Sleeper pick to win: Josh Berry
Kalshi probability: 4%

Josh Berry's career-best Top 10 streak reached six in a row at a testing Darlington course last week (seventh). It's hard to pass up these odds on a driver this hot regardless of venue.

Berry has had only two career starts at WWT Raceway, and they were both 36th-place finishes due to accidents. A left-front tire failed him in 2024, and last year Chase Elliott made contact with him and ended his day early.

I'm not holding those unlucky breaks against Berry, and will play him to 5%.

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Robert Criscola - Covers.com
Betting Analyst

Robert M. Criscola’s road to becoming a Covers publishing editor began with an internship at Metro New York, which eventually turned into a freelance job at MetroBet covering many sports from a wagering angle, including horse racing. He continued to focus on “The Sport of Kings” by writing for shapperdacapper.com, danonymousracing.com, and informer.fanxt.com before joining the team at the TwinSpires Edge in 2019 as a regular contributor and weekend editor. “Crisco” began writing game previews for Covers in 2022 and joined the editing team in 2023.

His best advice for sports bettors? Bet with your head, not over it.

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