Ty Dillon's upset run gives NASCAR its first-ever bracket 'Cinderella'

Ty Dillon used the bumper to fight his way closer to $1 million. Can the backmarker driver really pull off the upset?
NASCAR Cup Series Grant Park 165
NASCAR Cup Series Grant Park 165 | James Gilbert/GettyImages

Maybe a few-dozen people picked Ty Dillon to get out of the first round of NASCAR's in-season tournament.

Probably like 10 people picked Dillon, who has one top 10 in 2025, to get out of the second round (and those people probably did coin-flip brackets).

I'm relatively confident no one, not the fans, not employees of Kaulig Racing, probably not even Dillon himself, had Ty Dillon among the final four drivers in the $1 million challenge.

But here we are. And NASCAR has to be loving what he's brought to the table over the last month.

Dillon gets physical to claim massive bracket upset over Alex Bowman

Dillon came into the final lap this past weekend at Sonoma right behind his bracket adversary, Alex Bowman. Bowman is notedly good at road courses, Dillon is not. He's never finished inside the top 15 at a road course, while Bowman won at Chicago last season.

Dillon spent much of the day outside the top-20, but with some late restarts, the two were right next to each other going into the final turns.

Dillon lays the bumper to Bowman once without success, but heading into the final braking zone, Dillon sends the No. 48 off line, taking P17 and the transfer into the final four.

It was an unbelievable moment truly encapsulates the randomness of a head-to-head tournament in auto racing. It also gave Dillon something to celebrate over the radio about after a whirlwind couple of weeks for the backmarker driver.

Dillon goes from afterthought to Cinderella story

Dillon, for those who don't know much about him, has been kicking around in the Cup Series for a decade.

He has 264 Cup starts, no wins, and just eight top 10s. Six of those came at Daytona/Talladega/Atlanta, a.k.a drafting tracks where anyone can find their way to the front. Not to rag on the guy in a major moment of his career, but he has never been a standout talent.

Dillon got the boot from Spire Motorsports in 2023 after managing just five top 20s on the season (four at drafting tracks). Before that he spent time at Petty, Germain (RIP) and other teams, with his best-ever points finish being 24th in 2017.

He spent 2024 racing the the Craftsman Truck Series where he managed just two top 10s before stepping aside for the season's final four races. But he has somehow (somehow meaning, his grandfather is RCR team owner Richard Childress) made his way back to the Cup Series full-time in 2025.

Coming into the in-season tournament, Dillon was the 32nd and last car to qualify for the bracket field. His best finish all season was 12th at Texas.

Dillon gets another viral moment from his head-to-head win

Dillon was faced with top-seed Denny Hamlin in the opening round at Atlanta, a daunting task. But thanks to a massive wreck and a top 10 finish, he inexplicably moved on.

Rarely do we hear from Dillon during a live broadcast, but with a camera in his face, he delivered a tongue-in-cheek jab to Hamlin's famous villain moment.

Then up against Brad Keselowski in Chicago, Dillon advanced thanks to an early wreck that the No. 6 got caught up in. Dillon only needed a P20 finish to move on. Still, he was ready with a joke worthy of advancing.

Now with a slick piece of driving to get in the semifinal round, he faces off against John Hunter Nemechek for a spot in the finals.

And although TNT didn't speak to him post-race at Sonoma, he made sure when PRN gave him a radio interview, he made it 3-for-3 on sly comments about the teams he's defeated.

After doubting his abilities three weeks in a row, it's time to accept that anything can, and will, happen at Dover with the No. 10 Kaulig car.