In his Indy car debut at Walt Disney World Speedway, Stewart led 37 laps and finished a close second to fellow rookie Buzz Calkins.

For his Indianapolis 500 debut, he initially qualified on the outside of the front row, but the disqualification of Arie Luyendyk's time and the death of his teammate Scott Brayton a week later propelled Stewart to the pole position.

Between his time in USAC and the IRL, Stewart earned the nickname of "Smoke", first for slipping the right rear tire during dirt races and then for blowing his engine often during his 1997 championship run.

This time, he was racing for Joe Gibbs, NFL Hall of Fame head coach of the Washington Redskins, who was having major success with Bobby Labonte in the Winston Cup Series.

On August 16, 2005, Stewart was fined $5,000 and placed on probation until December 31 for hitting Brian Vickers after the completion of the Busch Series Zippo 200 at Watkins Glen.

The crash began on the back straightaway and also collected Bobby Labonte and his brother Terry, Rusty Wallace, Steve Park, Jason Leffler, Jerry Nadeau, Buckshot Jones, Andy Houston, Ward Burton, Mark Martin, Kenny Wallace, Jeff Gordon, Elliott Sadler, Dale Jarrett, Jeff Burton, John Andretti, and Robby Gordon.

Stewart took the worst of it, as his car turned backward after being hit by Ward Burton, pushed over Robby Gordon, then flipped twice in midair, hooked Bobby Labonte's hood, and came to a stop in the infield.

He got into much bigger trouble in the Pepsi 400 at Daytona, where he confronted a Winston Cup official after ignoring a black flag, which he had received for an illegal pass on Dave Blaney.

In January 2004, Stewart teamed with Andy Wallace and Dale Earnhardt Jr. in a Boss Motorsports Chevrolet to take fourth in the 24 Hours of Daytona sports car endurance race.

Stewart felt very sick during the race at Watkins Glen International and nearly withdrew from it due to food poisoning, stomach cramps, a headache, and a sinus infection.

Following his win in the Pepsi 400, Stewart began climbing the fence separating the fans from the race track after each victory, borrowing IndyCar Series driver Hélio Castroneves' trademark move.

[22] After winning the 2009 All-Star race, Stewart was quoted as saying "I'm too damn fat to be climbing fences," and recently purchased $17,000 worth of exercise equipment to remedy the problem.

Just a few days later, during the Daytona 500, Stewart was involved in several incidents with Jeff Gordon, Kyle Busch, and Matt Kenseth, whom he chased halfway across the track to run into the grass.

In addition, Stewart's three wins in the Chase races gave him five total for the season, tying him with Jimmie Johnson and Kevin Harvick for second-most in Nextel Cup behind Kasey Kahne's six.

In his first Car of Tomorrow race with the Impala SS, Stewart was dominant at Bristol, leading 257 of 504 laps (green-white-checker finish), before he experienced a fuel pump problem.

[33] After the Ford 400, Stewart attended a tearful farewell meeting with Joe Gibbs Racing and gave his car and team to rookie Joey Logano, who replaced him for JGR.

On August 15, 2008, fellow Indiana native Ryan Newman signed a multi-year contract to drive the second car for Stewart-Haas Racing, originally to be designated No.

On October 30, 2011, at Martinsville Speedway, Stewart won the Tums Fast Relief 500, leading three times for 14 laps and moving into championship contention in second place in the points standings.

On November 20, 2011, Stewart won the NASCAR Sprint Cup Series championship by winning the final race at Homestead-Miami Speedway while Edwards finished second.

After the race, Stewart, angered, confronted Logano, who had just wrecked his car after battling with Denny Hamlin hard into the last turn, on pit road in a scuffle involving both teams' crews.

[46] At Richmond, Stewart looked to be in contention for the win as he was 5th on a green-white-checkered finish, but in a fashion similar to his confrontation with Logano at Fontana; after a poor restart he lost a few positions.

After a spin early in the race, Stewart was running 12th at the last caution, coming off of pit road 2nd and lining up 4th for the green-white-checkered finish behind Paul Menard, his driver Kurt Busch, and Landon Cassill.

[59] At the end of the October Charlotte race, Stewart was hit on pit road by Brad Keselowski, who was trying to run into Matt Kenseth, but missed.

[62] Despite these results, Stewart refused to put the blame on his crew chief, in spite of criticism from fans, saying that "I still really like working with Chad Johnston, I don't feel like he's what's holding us back...

He was racing Aric Almirola hard, and Martin Truex Jr. cut in front of Tony, creating a hole in Stewart's bodywork which required him to pit for repairs.

[98]A couple of days after the announcement of his exoneration by Ontario County (N.Y.) District Attorney Michael Tantillo, Stewart told The Associated Press, that "I know 100 percent in my heart and in my mind that I did not do anything wrong.

"[99] After a few years of going through the process of the wrongful death lawsuit filed by the Ward family, it was announced in April 2018, that the suit had been settled out-of-court, just a few weeks before the trial was scheduled to begin.

[105] Stewart has won USAC car owner titles in the Silver Crown division in 2002 and 2003 with J. J. Yeley, in 2004 & 2005 with Dave Steele and 2010 and 2011 with Levi Jones of Olney, IL.

In July 2020, Stewart and former NASCAR crew chief Ray Evernham formed the Superstar Racing Experience (SRX), a stock car series that began in summer 2021.

It featured top drivers from NASCAR, IndyCar, NHRA, and World of Outlaws, including race winners Kenny Wallace, Carl Edwards, Jimmie Johnson, Clint Bowyer, Kyle Busch, and Stewart himself.