Has Tony Stewart ever won the Chili Bowl? All you need to know

Former NASCAR driver and owner, Tony Stewart, has competed in multiple racing competitions throughout his illustrious career, including the Xfinity Series, USAC's midget, sprint, and silver championships, and the IndyCar series.

He has also entered the Chili Bowl Midget Nationals multiple times and has won the competition twice, taking home the Golden Driller trophy on separate occasions, once in 2002, and his second in 2007.

Tony Stewart won his first Chili Bowl in the same year as he won his first Cup Series championship. The Indiana native scored his win at the 16th Annual edition of the main event after a battle with driver Kevin Doty for the lead of the race over the last 16 laps of the race. The former Stewart-Haas Racing driver finally won the battle in Lap 49, holding the lead until the finish line - where he went home with a $22,000 cash prize.

After making his debut in the Cup Series in 1999, the 2002 Midget Race was an opportunity for Stewart to race against drivers from his dirt racing background. Speaking about racing in the Bowl, he said:

"I miss racing with these guys ‘cause it’s fun,’’ Stewart said. "This style of racing is fun because you come here and unload your car and you race. You go out have dinner together and drag down the road to the next place and do it all over again next week. There is no politics. You didn’t once here anybody (Saturday) complaining about his body style had more downforce and less drag than anybody else. That’s why it’s fun. You don’t hear anybody complain about anything, you just go race.’’ [ via chilibowl.com]

His second win came well after he clinched his second Cup title and after a three-year break from competing at the Tulsa Expo Raceway. This time, Stewart was racing for his own racing enterprise, Tony Stewart Racing, and he was in one of five cars at the Chili Bowl under the banner.

Driving the #20 Spike Chassis, the Joe Gibbs Racing driver battled his way to the lead after starting fifth in the main event. Talking after winning his second Golden Driller with sponsor Chevrolet, Stewart said:

"To run one of my own cars and get my first win in one my own cars and most of all get our first win for Chevrolet in our first race since we switched sponsorships, I don't know how much better of a coming out party for a new sponsor you could have than to win the biggest Midget race of the year. To have the weekend that we had for Chevrolet like that, that's what I'm excited about." [via chilibowl.com]

Tony Stewart would race in the Chili Bowl Nationals three more times. He would only secure a Top 10 finish twice, with an eighth place and a tenth place finish in 2008 and 2012, but ended his run at the Midget Racing main event in 2013 with a 15th place finish.

Tony Stewart Racing celebrates its 25th anniversary in 2025

NHRA top fuel driver Tony Stewart during qualifying for the NHRA Finals at In-N-Out Burger Pomona Dragstrip. - Source: Imagn

Tony Stewart formed TSR in November 2000, beginning with just one World of Outlaws team. In its 25 years, TSR has won 14 USAC championships, 9 World of Outlaws titles, 5 Kings Royals wins, and has secured victory at the Knoxville Nationals 12 times.

Discussing his now 25-year-old racing team, Stewart said (via The Republic):

“When you look at what we’ve been able to accomplish since 2001 it makes you stop, reflect, smile and think of all the great things that we’ve been able to do as a group of talented drivers, crew members, crew chiefs and great partners along the way… it’s just been a great ride.”

Tony Stewart has been competing in NHRA drag racing since 2023, where he has won four races in the Top Alcohol series, finishing the season as the runner-up in the standings. In 2024, Tony moved up to the Top Fuel category, where he was named Rookie of The Year after his ninth-place finish in his debut season.