Stewart got his first competitive go-kart in Westport, Indiana in 1979 and won his first championship in 1980. He won a World Karting Association championship in 1987 before moving up to the United Midget Racing Association, racing TQ (three-quarter) midgets until 1991. He then joined the United States Auto Club (USAC) series with the help of karting sponsor and friend Mark Dismore, earning USAC Rookie of the Year in 1991. He became USAC National Midget Series Champion in 1994 and 1995 and claimed the USAC Silver Crown Series championship in 1995.
In 1995, Stewart became the first driver to win USAC's version of the Triple Crown, earning championships in the National Midget, Sprint, and Silver Crown divisions in a single season. His highlights that year included winning the Hut Hundred and the 4 Crown Nationals.
Stewart entered Indy car racing in 1996 with Team Menard in the newly formed Indy Racing League. In his debut at Walt Disney World Speedway, he led 37 laps and finished second to fellow rookie Buzz Calkins. For the Indianapolis 500, he initially qualified on the outside of the front row; the disqualification of Arie Luyendyk's time and the death of teammate Scott Brayton propelled him to pole position. He led 44 laps before a malfunctioning pop-off valve ended his race.
He won his first IRL race at Pikes Peak in 1997, leading all but seven laps of a 200-lap event, and went on to beat Davey Hamilton for the IRL championship that year despite finishing seventh, fourteenth and eleventh in the final three races. In 1998, he won twice and finished third in the championship. He made his NASCAR Busch Series debut in 1996 for car owner Harry Rainer, with a best finish of 16th in nine starts.
Between 1997 and 1998, he earned the nickname "Smoke" — first for slipping the right rear tire on dirt, and later for frequently blowing his engine during his 1997 championship run. He raced part-time in the Busch Series for Joe Gibbs Racing in 1998, finishing in the top five five times in 22 starts and coming close to a first win at Rockingham before being beaten on the last lap by Matt Kenseth.
Stewart moved to the Cup Series full-time in 1999 driving the No. 20 The Home Depot-sponsored Pontiac for Joe Gibbs Racing. He qualified on the outside pole for the 1999 Daytona 500 and set a series record for wins by a rookie with three — at Richmond, Phoenix and Homestead — surpassing Davey Allison's record set in 1987 (Stewart's record held until 2025). He finished fourth in the points standings, also claiming Rookie of the Year.
In 2000, Stewart won six races including both Dover races, Michigan, Martinsville, New Hampshire and Homestead, but fell to sixth in the standings. In 2001, he won three more races at Richmond, Infineon and Bristol and finished second to Jeff Gordon in the points. On Memorial Day weekend 2001, he ran both the Indianapolis 500 and the Coca-Cola 600, completing all 1,100 miles by finishing sixth at Indianapolis and third at Charlotte.
Stewart started inauspiciously, blowing his engine at Daytona after two laps, but built momentum through the second half of the season. A $50,000 fine and 25-point deduction following an altercation with a photographer after the Brickyard 400 did not derail him. He won the following week at Watkins Glen — despite later revelations that he had jumped the restart — then put together a streak of consistent top-ten finishes to claim the points lead at Talladega and hold off Mark Martin for his first Winston Cup championship.
Stewart won at Pocono and Charlotte in 2003 and finished seventh in the points. Joe Gibbs Racing switched from Pontiac to Chevrolet that year. In January 2004, he teamed with Andy Wallace and Dale Earnhardt Jr. at the 24 Hours of Daytona for Howard-Boss Motorsports, leading 355 of 526 laps with a five-lap advantage before mechanical problems brought a fourth-place finish with less than 20 minutes remaining. That November, Stewart purchased Eldora Speedway, a half-mile dirt track in New Weston, Ohio, which he had first raced at in 1991.
Stewart won five races in 2005 — at Infineon, Daytona, New Hampshire, Watkins Glen (giving him three consecutive road course wins) and Indianapolis, his hometown track. After borrowing Hélio Castroneves' fence-climbing tradition following victories, he entered the Chase as the No. 1 seed and won his second title on November 20, 2005. He was one of the youngest drivers to win multiple championships at 34. His total 2005 earnings were $13,578,168, including $6,173,633 for the championship, the largest season total in NASCAR history to that point.
Stewart missed the 2006 Chase — the first defending champion to do so — finishing eleventh in points despite winning three Chase-period races at Kansas, Atlanta and Texas. He also won the IROC championship that season, taking two of the four events. In 2007 he recorded his thirtieth career Cup win at the USG Sheetrock 400 at Joliet and won the Brickyard 400 for a second time. Joe Gibbs Racing switched manufacturer partnerships from Chevrolet to Toyota for 2008.
Stewart won his sole race of 2008 at the AMP Energy 500 at Talladega after NASCAR ruled that race leader Regan Smith had made an illegal pass under the yellow line. In July 2008 he agreed a deal with car owner Gene Haas to form a co-ownership partnership, and was released from the final year of his JGR contract. He finished his JGR career with 33 wins and two championships, third-most successful behind Kyle Busch and Denny Hamlin.
Stewart took 50% ownership of what became Stewart–Haas Racing, driving the No. 14 Chevrolet — a number chosen as a tribute to his hero A. J. Foyt. He became the highest-paid NASCAR driver at the time. Ryan Newman signed to drive the second car, the No. 39, with U.S. Army sponsorship.
In 2009, Stewart won his first race as driver/owner at Pocono, the first owner-driver to win in the Cup Series since Ricky Rudd in 1998. He also won the non-points NASCAR Sprint All-Star Race and the Coke Zero 400 at Daytona. He qualified for the Chase by leading the standings after 26 races, ultimately finishing sixth.
Stewart entered the 2011 Chase winless but won the opening Chase race at Chicagoland Speedway. He won at New Hampshire after Clint Bowyer ran out of fuel, and added wins at Martinsville and Texas Motor Speedway. He claimed the championship at the final race at Homestead-Miami Speedway by winning the event while Carl Edwards finished second — they finished tied on total points, but Stewart claimed the tiebreaker with five wins to Edwards's one. He became the first owner-driver to win the Cup championship since Alan Kulwicki in 1992.
Stewart won three races in 2012 and finished ninth in the championship. In 2013, he won at Dover in a green-white-checkered finish, extending his consecutive season win streak to fifteen, but broke both his tibia and fibula during a sprint car race at Southern Iowa Speedway in Oskaloosa, Iowa on August 5, ending a streak of 521 consecutive Cup starts dating to the 1999 Daytona 500. Mark Martin substituted for the final thirteen races. Stewart ended 2014 without a win — his worst statistical season as a driver — though the team claimed the Owner's Championship with Kevin Harvick driving.
On August 9, 2014, Stewart competed in an evening sprint car race at Canandaigua Motorsports Park in Canandaigua, New York. Stewart bumped Kevin Ward Jr., causing Ward to spin into the wall. Under a full-course caution, Ward exited his car and charged down the track; as Stewart approached, Ward lunged at the car and was struck by its right rear tire, suffering fatal injuries. Ward was pronounced dead on arrival at Thompson Hospital due to "massive blunt trauma." Stewart skipped Watkins Glen and the following two Cup races, replaced by Regan Smith and Jeff Burton. A grand jury declined to indict Stewart on manslaughter or criminally negligent homicide charges. The civil wrongful death suit filed by Ward's family was settled out of court in April 2018.
Stewart failed to score a win in 2015, missing the Chase for the second straight year. On January 31, 2016, he injured his back in a dune buggy accident outside San Diego with Greg Biffle, suffering a burst fracture in his lumbar vertebra. He missed the first eight races. He returned at the Toyota Owners 400 at Richmond on April 24, 2016, and won at Sonoma in June — his only win of the season and his first in three years — from a last-lap pass on Denny Hamlin. Stewart finished in the Chase before being eliminated in the first round. He retired with a 22nd-place finish at the 2016 Ford EcoBoost 400, ending an eighteen-year Cup career with 49 points-paying victories, ranking him thirteenth on the all-time NASCAR Cup winners list.
Stewart co-founded the Superstar Racing Experience (SRX) with former crew chief Ray Evernham in July 2020. Competing full-time in the inaugural 2021 SRX season, he swept the two dirt track events at Knoxville Raceway and Eldora and won the championship by 45 points over Ernie Francis Jr.
In January 2025, Stewart purchased the All Star Circuit of Champions from Guy Webb. He also merged the Renegade Sprint Series into the All Stars for the 2015 season, and as of 2026 plans to run the High Limit Racing series with Rico Abreu.
In December 2023, it was announced that Stewart would drive an NHRA Top Fuel dragster in 2024, replacing his wife Leah Pruett, who stepped aside to start a family. He claimed his first Top Fuel win at the 2025 Four-Wide Nationals at Las Vegas Motor Speedway. On January 13, 2026, Kaulig Racing announced that Stewart would drive the No. 25 Ram 1500 in the Truck Series at Daytona — his first Truck race since 2005.
Stewart–Haas Racing fielded up to four cars and won two Cup championships — Stewart's 2011 title as driver/owner and Harvick's 2014 title. On May 28, 2024, the team announced it would shut down at the end of the 2024 season. Gene Haas later announced he would keep one charter and restructure as Haas Factory Team.
Stewart purchased Eldora Speedway in late 2004 from Earl Baltes. He also co-owns Paducah International Raceway and Macon Speedway in Illinois. His Tony Stewart Racing team has won World of Outlaws Sprint Car Series championships as an owner with Donny Schatz in 2008–2009, 2012 and 2014–2018. The Tony Stewart Foundation, founded in 2003 to support chronically ill children and injured motorsports drivers, announced its closure in October 2024.
Stewart competed in the Rolex 24 at Daytona five times between 2002 and 2007, all for Howard-Boss Motorsports except 2002 when he drove for the Crawford factory team with Jan Lammers and Johnny Mowlem. His best result was third place in 2005 with Jan Lammers and Andy Wallace, after the team had been leading with under two hours remaining when a broken gearbox ended their lead.
Stewart was inducted into the NASCAR Hall of Fame on January 31, 2020 (voted in May 22, 2019). He was also inducted into the Indianapolis Motor Speedway Hall of Fame in 2018, the National Midget Auto Racing Hall of Fame in 2001, and the National Sprint Car Hall of Fame in 2022. He received the Richard Petty Driver of the Year award in 2002, 2005 and 2011. He is the only driver to win the Cup Series championship under the old points system and the Chase playoff format, and the only driver to win the title under three different title sponsorships — Winston in 2002, Nextel in 2005 and Sprint in 2011. He is also the first driver in the Cup Series to win the championship by a tiebreaker. Stewart is the all-time winningest Cup driver at Chicagoland Speedway (three wins), Homestead-Miami Speedway (three wins, tied) and Watkins Glen International (five wins).
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