5 match-ups to look out for at NASCAR Chicago race ahead of $1,000,000 challenge’s round 2

The second round of NASCAR's In-Season Challenge will take place on the streets of Chicago this weekend with a strong list of contenders. Several favorites were out of the bracket following multi-car wrecks at EchoPark Speedway last week.

The In-Season Challenge is a 32-driver, single-elimination tournament with a $1 million prize money. The mid-season tournament, covered by the returning TNT Sports, is scheduled for five races, including the championship match in the Brickyard 400 at Indianapolis Motor Speedway.

For now, the second round is upon us, with 16 drivers left in the fight for the million-dollar reward. Read on to learn about our top five match-ups to look out for this weekend.

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1. Chase Elliott (#5) vs John Hunter Nemechek (#12)

All eyes are on Chase Elliott following his first win of the 2025 NASCAR season at EchoPark Speedway last week. He defeated Austin Dillon in the opening round and will face 12th-seeded John Hunter Nemechek in the second round.

Chase Elliott locks himself in the second round after winning the Quaker State 400 - Source: Getty

While Elliott looks like the favorite on paper, last week's race showed that anything is possible. Notably, the top-seeded drivers were out of the contention, including Denny Hamlin, Chase Briscoe, Christopher Bell, and Ryan Blaney.

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2. Alex Bowman (#8) vs Bubba Wallace (#9)

Another driver to look out for is Alex Bowman. The #48 Hendrick Motorsports driver is the defending Chicago street race winner, which should challenge Bubba Wallace, who is also fighting to secure a playoff spot with eight regular-season races remaining.

Alex Bowman won the 2024 Grant Park 165 - Source: Imagn

Bowman and Wallace are pretty even in the NASCAR Next-Gen car era stats-wise. They also follow each other in the points standings (12th and 13th), making it tougher to predict who will advance to the third round.

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3. Ryan Preece (#15) vs Noah Gragson (#31)

Former Stewart-Haas Racing teammates Ryan Preece and Noah Gragson are set to face off in the second round of NASCAR's In-Season Challenge. Gragson is carrying a strong momentum after beating the second-seeded Chase Briscoe in the opening round last week.

Ryan Preece (#60) and Noah Gragson (#4) during the 2025 Daytona 500 - Source: Getty

In terms of head-to-head results this year, the #60 RFK Racing driver has the upper hand, finishing ahead of his opponent 14 times in 18 races. But on the streets of Chicago, the Ford drivers are even.

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4. Tyler Reddick (#23) vs Carson Hocevar (#26)

Tyler Reddick is one of the favorites to win in the Grant Park 165. However, his second-round opponent, Carson Hocevar, is no slouch. Hocevar has had strong finishes here and there, including two second-place finishes this year (Atlanta and Nashville).

Tyler Reddick on the streets of Chicago in 2023 - Source: Imagn

Moreover, the sophomore NASCAR driver has been making headlines for aggressive driving, resulting in run-ins with fellow competitors, such as Ricky Stenhouse Jr. If Reddick and Hocevar find themselves competing against each other for a chance to advance to the next round, their match-up should be a fun one to watch.

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5. Ty Gibbs (#6) vs AJ Allmendinger (#22)

Ty Gibbs is another driver entering the Chicago street race with a promising track record. He has the most points in the venue thanks to his back-to-back top-10 finishes. His opponent, meanwhile, is AJ Allmendinger, who has the advantage in terms of experience.

Ty Gibbs is one of the top drivers in the Chicago street race - Source: Imagn

Allmendinger secured a second-round spot after an upset, winning over the 11th-seeded Michael McDowell. The two veteran NASCAR drivers made last week's pre-race ceremony fun, playfully beating each other during the introduction.