By David Morgan, Associate Editor
CHICAGO – After a chaotic start to the NASCAR In-Season Challenge, which knocked out several top contenders, the second round of the season within a season that will pay $1 million to the winner after five races rolls into Chicago and Sunday’s running of the NASCAR Chicago Street race.
The original field of 32 has now been cut to 16, with only one driver that has won a race still alive for the big prize – last weekend’s winner at Atlanta, Chase Elliott.
Here is a breakdown of where things stand heading into Sunday, and who the likely driver will be to move on to Sonoma still in the running for the money.
Matchup No. 1
- Ty Dillon (No. 32 seed) vs Brad Keselowski (No. 17 seed)
Ty Dillon advanced to the second round over Denny Hamlin after Hamlin was involved in the big one at Atlanta, poking fun at his fallen opponent after the race, saying:
“All you Denny fans out there, I just knocked out your favorite driver,” he said.
Meanwhile, Brad Keselowski fell just short of winning the race, losing the lead to eventual winner Chase Elliott, but took the consolation prize of moving on to the second round over Kyle Busch.
Heading into Chicago, Keselowski should have a leg up on Dillon. While his results on the streets don’t show it, Keselowski and RFK Racing as a whole have been on the upswing as of late, so look for the driver of the No. 6 Ford to win out on this matchup and move on to the next round at Sonoma.
Advantage: Keselowski
“It should be good,” Keselowski said of his match-up with Dillon. “I haven’t paid a lot of attention to it. Ty’s a really good road course driver in the rain specifically. So, it’ll be an epic battle.”
Matchup No. 2
- Alex Bowman (No. 8 seed) vs Bubba Wallace (No. 9 seed)
Bowman enters Chicago on the heels of a third-place finish at Atlanta and as the defending winner in Chicago, having come away triumphant in this race one year ago. As the lone Hendrick Motorsports driver without a win, look for Bowman to be on the chip Sunday as he aims for back-to-back wins in Chicago and a trip to the Playoffs.
Wallace was able to surpass Daniel Suarez last weekend in Atlanta after Suarez was caught up in a crash, but coming into Chicago, it will be a tall task for Wallace with road courses being his Achilles heel throughout his Cup career.
Only three times has Wallace finished inside the top-10 on a road course, with a seventh and a ninth-place finish on the Charlotte Roval in 2022 and 2024, respectively, as well as a fifth-place finish on the Indianapolis Motor Speedway Road Course in 2022.
Adding another interesting element to the match-up between these two at Chicago, specifically, is the run-in they had here last year as Bowman was en route to the win.
Advantage: Bowman
“Maybe we’ll get on stage and, like, fake fight like AJ and Michael did last week,” Bowman joked. “But, no, I think he and I are totally good. But yeah, I mean, he’s been really fast here in the past. Like, you don’t tend to think of him as a road course guy, but here last year, he was really fast. So, definitely going to be a tough one.
“But yeah, I think, you know, adding excitement, it’s probably more for the fans, right? And from where I sit, like, I just try to go to work and do the best I can throughout the weekend and kind of not super focused on it. Obviously, I think if we get down to the final round, you’ll probably fixate on it a little bit more. But if it gives the fans something to talk about and be excited about, I think it’s really good.”
Matchup No. 3
- John Hunter Nemechek (No. 12 seed) vs Chase Elliott (No. 5 seed)
With the momentum of a home track win at his back, Elliott should be the favorite in this matchup, especially in the superior Hendrick Motorsports equipment vs Nemechek and Legacy Motor Club.
Nemechek finished sixth in the race at Mexico City earlier this season, a race in which Elliott finished on the podium in third. Couple that with seven road course wins throughout his career and it should be a no-brainer that Elliott would get the nod in this matchup.
Comparing Chicago stats to Chicago stats, Elliott also takes the advantage, having finished third in the inaugural street race and 21st a year ago, while Nemechek finished 35th in his lone Chicago start a year ago.
Advantage: Elliott
“We’ve just been doing this long enough to know it all kind of starts and ends with us,” Elliott said of the current performance of the No. 9 team after their win a week ago. “We have to make sure we’re doing our part and I’m doing my part. Just bringing everything I can possibly bring every single week. It’s the honest conversations that we have on Monday mornings that are either going to make us better or make us fail. All of the pieces of the puzzle are there.
“We’re working on the right things. I think I’m asking for the right things out of the car. I’m really proud of our team for just sticking together. I think there’s been so many times that we could have thrown in the towel and really kind of fractured from the inside. It’s a really important thing for me to have climbed that mountain and stood on top of it with AG (Alan Gustafson) and we’ve kind of fallen off that hill.
“Getting back to the top with him and with our group and doing it together, I think is a really important thing to do. We have so much respect for one another as a team that we’re going to continue to make each other better as we push forward.”
Matchup No. 4
- Erik Jones (No. 20 seed) vs Ricky Stenhouse, Jr. (No. 29 seed)
This one could be a toss-up certainly, with neither driver being especially great on road courses, but Jones would seem to be the pick here over Stenhouse.
With Legacy Motor Club getting their feet under them the longer into the season we get, the steady Jones just keeps plugging away, with his best finishes of the season coming in the last two months and climbing to 15th in the standings after a top-five at Atlanta last weekend.
Though his road course stats aren’t the greatest, having not finished inside the top-10 on a road course since August of 2022, if he can keep a steady wheel on Sunday, he should be able to win out in this matchup.
Stenhouse, meanwhile, has been hit or miss this season, and like Jones, finds himself on the outside looking in when it comes to the Playoffs. Road course wise, his best finish came in this race a year ago with a sixth-place result. If he can channel the Stenhouse of a year ago, he has a chance, but Jones still holds the advantage for now.
Advantage: Jones
“Making it out of Atlanta was a challenge for anybody. Yeah, it’s pretty cool. Just to still be in it, right? I mean, half the guys are knocked out, so feel good about going up against Ricky (Stenhouse Jr.),” said Jones.
“I feel like that’s a doable one for us this weekend. Next week (is) Sonoma, (and that’ll) either be No. 42 (John Hunter Nemechek) or the No. 9 (Chase Elliott), and if it’s the No. 9, that’ll be a tough one for us. He’s probably going to run really well. So, either way, it’s fun to still be in it, have a shot. We’ll see where it goes.
“Like I’ve said, we’re in a long stretch of races right now and to have something other than the Playoff line to focus on I think is pretty cool for the sport. Fun to follow along and even when we fall out, if we fall out, it’ll be fun to follow until the end.”
Matchup No. 5
- Noah Gragson (No. 31 seed) vs Ryan Preece (No. 15 seed)
Give the nod to Preece in this one. RFK Racing as a whole has shown wholesale improvement this year, with Preece right there alongside his teammates Brad Keselowski and Chris Buescher. In recent road course races, Preece started on the front row at Mexico City before finishing 15th and finished ninth at Watkins Glen last season.
For Gragson, he hasn’t been bad on the road courses by any means, scoring his best road course result of eighth at Circuit of the Americas earlier this year. This one could certainly be a toss-up, but the momentum that RFK has at the moment should be enough to carry Preece ahead on Sunday.
Advantage: Preece
“I feel really good, honestly, about where we are as a team on road courses,” said Preece. “It’s been good. In the race we ran really well at COTA and we carried that over to Mexico and just with the weather and a lot of uncertainty and that penalty, we were still able to drive forward to 15th from 33rd.
“So, I feel really good about it and, you know, hopefully being able to capitalize this week as well as at Sonoma.”
Matchup No. 6
- Carson Hocevar (No. 26 seed) vs Tyler Reddick (No. 23 seed)
Reddick should be the clear winner here, with three road course wins under his belt and a runner-up finish in this race a year ago. Not to mention countless other top-fives and top-10s on road courses throughout his career.
As the best of the rest, the top driver in points without a win yet in 2025, there is no doubt that Reddick will be looking to finally make a visit to Victory Lane this year and do it in the city that idolizes 23XI Racing co-owner Michael Jordan.
Compare that to the wild man himself, Carson Hocevar, who has shown flashes of brilliance, but has also made a lot of enemies along the way. His best road course finish came with a third-place finish at Watkins Glen last year, but most likely will fall short of surpassing Reddick on Sunday afternoon.
Advantage: Reddick
“Between the last two years, we’ve been really good here. So, I certainly feel good about what my technique and craft is like,” said Reddick. “Unfortunately, though the whole field is able to look at what each driver does in preparation. I’d say we’re close. We’ll have a great shot at it.”
Matchup No. 7
- AJ Allmendinger (No. 22 seed) vs Ty Gibbs (No. 6 seed)
Another toss-up on the board. Logic would seem to point to Allmendinger being the favorite with his prowess on road courses, but Gibbs showed out at Mexico City, being one of the few to challenge eventual winner Shane van Gisbergen before he went on to dominate the latter stages of that race.
If that Ty Gibbs shows up on Sunday, it could be a challenge, but the experience of Allmendinger on these types of tracks should allow him to win out. His road course stats are second to none, with three wins on road courses and numerous top-fives and top-10s on his resume.
However, Chicago hasn’t been the greatest for Allmendinger in the first two years, with finishes of 17th and 38th, respectively. Allmendinger noted as much ahead of practice and qualifying on Saturday, explaining that his focus is just getting better here and if he is able to accomplish that, the rest will take care of itself.
Advantage: Allmendinger
“Well, I haven’t beaten many people on this racetrack for the last two years,” Allmendinger said with a laugh.
“I mean, I don’t need to worry about him. I gotta worry about myself and our race team, me just getting better around this racetrack. I probably haven’t run a lap or a handful of laps where I thought, okay, that’s where I feel really good about it.
“So, I don’t worry about other guys, you know, whether we’re racing one guy or, you know, we’re racing the other 39. My mindset especially today is just trying to be better and actually leave practice and qualifying being comfortable because I have yet to do that here. So, that’s all I’m focused on.”
Matchup No. 8
- Zane Smith (No. 14 seed) vs Chris Buescher (No. 3 seed)
Give this one to Buescher. Having won at Watkins Glen last season and scored several top-five and top-10 finishes throughout his career, road courses have become the best tracks for the driver of the No. 17 RFK Racing Ford and that should continue Sunday at Chicago.
Meanwhile, Zane Smith has struggled on road courses, banking only one top-five finish in all of his road course starts, finishing fifth at Watkins Glen a year ago. Barring disaster, Buescher should win out in this one easily.
Advantage: Buescher
“You know what, for the teams and drivers there’s real money in this thing, so we’re not blind to it, but it’s also not changing our approach to our race weekends,” Buescher said of balancing the in-season challenge with still trying to make it into the Playoffs.
“It’s not changing what happens in a race for us, so I don’t believe that is going to affect what you see from us. I think that ultimately at the end of the day the bigger picture is winning races, which brings on playoff implications and all of that leads to much bigger consequences for our organization. That is definitely the focus.”
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