NASCAR
Current NASCAR Cup Series Drivers with Past Wins at Chicagoland Speedway
Across its 19-year history before falling silent the last seven seasons, Chicagoland Speedway saw 13 different drivers celebrate as NASCAR Cup Series winners. This list includes champions, Hall of Famers, and some of modern NASCAR’s most defining drivers. Of those 13 previous Joliet winners, three of them will be in Sunday’s field. This trio fittingly represents all three manufacturers from three of NASCAR’s most storied teams. Here are the men who have tamed The Magnificent Mile and a Half before and hope to repeat their success.
Brad Keselowski
Bad Brad Keselowski holds the distinction of being one of only five drivers with multiple Chicagoland Speedway trophies. These victories came in a three-year span during his Cup championship (2012) and amid BK’s winningest season (2014). Both years saw the Penske No. 2 dominate in The Windy City but blow by someone who led more laps.
A fitting microcosm of that year’s Chase, 2012’s Chicagoland race saw Keselowski get the upper hand late over Jimmie Johnson. Meanwhile, 2014 saw a very competitive back-and-forth battle between the 2, Jeff Gordon, then-rookie Kyle Larson, and Kevin Harvick. Thanks to a bold three-wide middle pass in the closing laps, BK took Chase race one for a second time.
Entering 2026’s Chicagoland date, Keselowski is in desperate need of positive momentum. The No. 6 hasn’t been better than 15th since Texas in May, recently seeing four-straight sub-30th place results. These summer doldrums have seen the past Chicagoland winner plummet to 18th on The Chase grid. Including both of his wins, Keselowski has an active nine-race top-10 streak in Joliet. The veteran will be eyeing to extend that streak this weekend.
Brad Keselowski’s No. 6 BuildSubmarines.Com Ford Mustang on the grid from Charlotte Motor Speedway before the Coca-Cola 600 on Sunday, May 24, 2026. Photo Credit: Peter Stratta/TSJSports
Denny Hamlin
Entering Chicagoland Speedway as the Cup Series points leader, Denny Hamlin conquered this track in 2015’s Chase opener. Chicagoland saw Hamlin get by Jeff Gordon on a late restart to collect his 26th career Cup triumph. This victory came less than two weeks after Hamlin tore his right ACL playing basketball. Chicagoland also propelled Hamlin onwards to the Round of 12.
11 years later, Hamlin now heads back to this track as a team co-owner and championship rival with Chicago sports icon Michael Jordan. Trash talk and internal pressure between Hamlin and 23XI Racing could be very high this weekend. Each owner will be gunning for a very pivotal win near MJ’s home court. Sonoma last week saw Tyler Reddick relinquish the championship lead for the first time all season to Hamlin. The 11 now heads the Cup standings by one point. The Nos. 11 and 45 have each visited victory lane on similar intermediate ovals already this season. Reddick has never ran a Cup race at Chicagoland. Hamlin, meanwhile, has a .500 top-10 record here across 14 career starts.
Also taking part in a recent Goodyear tire test on the aged asphalt, the ball appears to be in Hamlin’s court at Chicagoland. Do not be surprised to see another 11 vs. 45 battle like we saw at Kansas and Texas. Another full court press weekend could be in store from the 11, trying to reclaim a track he’s taken before.
Denny Hamlin’s No. 11 National Debt Relief Toyota Camry on the grid from Charlotte Motor Speedway before the Coca-Cola 600 on Sunday, May 24, 2026. Photo Credit: Peter Stratta/TSJSports
Alex Bowman
Chicagoland Speedway’s most recent victor, June 2019 saw career win number one for Alex Bowman. Under the Illinois lights that night, the Hendrick Motorsports driver got by and held off future teammate Kyle Larson. Bowman led a fitting 88 laps for his maiden Cup win in the No. 88, and hopes to keep his title as Chicago’s master. Funnily enough, Bowman’s most recent win also came in The Windy City, but on the downtown streets over 2024’s July 4th weekend. The only man to win on both Chicago courses, Bowman is beaming at the opportunity to run it back on such a fun racetrack.
“It feels like a really long time ago,” Bowman said. “I’m definitely looking forward to getting back there. I think that race was super fun. Obviously, back and forth with Larson at the end was really cool. To get my first cup win up against Kyle and kind of as hard as it was, back and forth, losing the lead, getting it back. That was really special.”
“And then yeah, I just think it’s going to be tricky with the Next Gen Car. Like, that place is slick, so you’re going to be sliding around a lot. The Next Gen Car is just inherently hard to slide much without it getting away from you. It’s very bumpy, and Next Gen is tough through the bumps. So it’ll be interesting to see how the track widens out. Kind of what grooves are and aren’t at play because of the bumps and see what works. It’s kind of fun to go to a place without a huge notebook. I’ll be in the sim tomorrow morning. So I don’t really have any idea yet on how it’s going to drive other than talking to Kyle from the test. But yeah, looking forward to the challenge.”
“I think it’s a great racetrack. It certainly deserves a Cup race and I’m excited to see how it races with Next Gen. I think it’s going to be a challenge for sure. But yeah, excited to see it come back. Obviously haven’t been there since we won there. So I think it’ll be cool to to get to go there again. Kind of bring back some of those memories and yeah, glad I didn’t kill it for everybody.”
The Hendrick No. 48 does carry a bit of momentum into Chicagoland, fresh off a 10th-place Sonoma outing. That marked Bowman’s best result since back-to-back third-place runs at Talladega and Texas in May. Sonoma also saw Bowman break back into the top-30 in points for the first time since returning to the 48. In short, Bowman is positioned nicely for another breakout run around Chicagoland.
Alex Bowman’s No. 48 Ally Chevrolet Camaro on the grid at Bristol Motor Speedway before the Food City 500 on Sunday, April 12, 2026. Photo credit: Peter Stratta/TSJSports
Getting ready to see its first green flag in over seven years, nearly half of Sunday’s grid will make their first Cup start at Chicagoland Speedway. This track’s surface was aged, abrasive, and tore up tires 10 years ago. There’s no telling just how volatile and unforgiving it will be on Sunday. The eero 400 will go green at 6 p.m. ET on TNT, MRN, and SiriusXM NASCAR Radio. When the checkers fly Sunday night, these three drivers all hope to be out front, but 36 others will try to keep them at bay.
Written by Peter Stratta
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Photo credits to Jared C. Tilton/Getty Images
