Career Timeline of Tony Stewart: Major Achievements and Milestones

From career breakthroughs to professional milestones, explore how Tony Stewart made an impact.

Tony Stewart, nicknamed "Smoke", is a semi-retired American professional auto racing driver and former NASCAR team co-owner. He achieved significant success in NASCAR, securing four Cup Series championships. Two wins as a driver and another as a driver/owner, plus a further owner's title demonstrate Stewart's impact on the sport as both a competitor and a team owner. Currently, he competes in the NHRA Top Fuel class, showcasing his continued passion for auto racing.

Sections (6)

Full Timeline Early Life & Education Career & Achievements Success & Recognition Challenges & Struggles Controversies & Scandals

1966: Rookie Record

In 1966, James Hylton finished 2nd as a first-timer, only bested Tony Stewart's Rookie Record.

1979: First Go Kart

In 1979, Tony Stewart got his first competitive go kart in Westport, Indiana, marking the beginning of his racing career.

1980: First Championship

In 1980, Tony Stewart won his first championship, demonstrating his early talent in racing.

1987: World Karting Association Championship

In 1987, Tony Stewart won a World Karting Association championship, showcasing his success in go-kart racing.

1987: Breaking Rookie Record

Tony Stewart surpassed Davey Allison's record set in 1987 for the most wins by a rookie with three.

1991: Moved Up to UMRA and USAC Series

In 1991, Tony Stewart moved up to the United Midget Racing Association (UMRA) and then to the United States Auto Club (USAC) series, progressing in his racing career. He was also named USAC Rookie of the Year.

1994: USAC National Midget Series Champion

In 1994, Tony Stewart was crowned USAC National Midget Series Champion, marking a significant achievement in his career.

1995: USAC Triple Crown Winner

In 1995, Tony Stewart became the first driver to win USAC's version of the Triple Crown, earning championships in National Midget, Sprint, and Silver Crown divisions.

1995: USAC National Midget and Silver Crown Series Champion

In 1995, Tony Stewart won the USAC National Midget Series Champion, and USAC Silver Crown Series champion, continuing his successful trajectory in racing.

1996: Struggles to Finish IRL Races

During the 1996-97 IRL season, Tony Stewart struggled to finish races, failing to complete the first three events on the schedule. He came in second at Phoenix.

1996: Competed Part-Time in NASCAR Busch Series

In 1996, Tony Stewart competed part-time during the NASCAR Busch Series season with the team, marking his initial involvement in the series.

1996: Indianapolis 500 Debut and NASCAR Busch Series Debut

In 1996, Tony Stewart debuted at the Indianapolis 500, starting from pole position. The same year, he made his NASCAR Busch Series debut for Harry Rainer, and also had a Truck Series ride with Mueller Brothers Racing.

1996: Indy Car Debut with Team Menard

In 1996, Tony Stewart debuted in Indy car racing with Team Menard, finishing second at Walt Disney World Speedway and leading 37 laps. He signed for Team Menard as a last-minute addition for the abridged three-race initial season, after unsuccessful negotiations with A. J. Foyt Racing

1997: Planned Move to Winston Cup Series Falls Through

In 1997, Tony Stewart had planned to move up to the Winston Cup Series but the deal fell through when Stewart decided he was not yet ready for the move.

1997: First IRL Career Win at Pikes Peak and Series Championship

In 1997, Tony Stewart secured his first career win at Pikes Peak, leading almost the entire race. He won the IRL title, beating Davey Hamilton.

1998: USAC Finishes and Copper Classic Wins

In 1997 and 1998, Tony Stewart finished thirteenth and eleventh in the USAC national points, and won the Copper Classic both years. During this period he earned the nickname "Smoke".

1998: Continued Busch Series Races and IRL Season

In 1998, Tony Stewart continued racing in the Busch Series for Joe Gibbs and had success in both the Busch Series and IRL, winning twice and finishing 3rd in the IRL championship.

1999: Drove No. 20 Joe Gibbs Racing Car

From 1999, Tony Stewart drove the No. 20 Joe Gibbs Racing car with The Home Depot as the primary sponsor.

1999: Formation of Tri Star Motorsports

In 1999, Tony Stewart co-owned Tri Star Motorsports, an IRL team, with Larry Curry, Andy Card, and Rick Ehrgott.

1999: Attempted 1,100 Miles on Memorial Day Weekend

In 1999, Tony Stewart competed in both the Indy 500 and the Coca-Cola 600, finishing in the Top 10 in both races.

1999: Consecutive Sprint Cup Starts Streak

In 1999, Tony Stewart started a streak of 521 consecutive Sprint Cup starts at the Daytona 500, which ended after his leg injury in 2013.

1999: NASCAR Cup Debut

In 1999, Tony Stewart started his NASCAR Cup career, qualifying for the Daytona 500 and battling with Dale Earnhardt for the lead in the Gatorade Twin 125s. Stewart drove the No. 20 The Home Depot-sponsored Pontiac.

1999: Moved to Cup Ride

In 1999, Tony Stewart was moved up to a Cup ride for the season after strong performance in the Busch Series, ending his full-time IRL career.

2000: Statistically Worse Season

In 2001, statistically Tony Stewart had a worse season than 2000, but he finished 2nd to Gordon in the final points standings.

2000: Six Wins and On-Track Incidents

In the 2000 NASCAR Winston Cup Series, Tony Stewart won six races but finished 6th in the standings due to DNFs and increased competition. He also had an incident with Jeff Gordon at Watkins Glen.

2001: Involved in 18-Car Crash at Daytona 500

During the 2001 Daytona 500, Tony Stewart was involved in an 18-car crash and was transported to Halifax Medical Center. He recovered to win three more races and finished 2nd in the points standings.

2001: Tri Star Motorsports

From 1999 to 2001, Tony Stewart co-owned Tri Star Motorsports.

2001: Controversies, Fines, and Probation

In 2001, Tony Stewart faced several controversies, including retaliating against Jeff Gordon at Bristol and confronting a Winston Cup official at Daytona for ignoring a black flag. He also had an incident with a Winston-Salem Journal reporter and confronted an official at Talladega for refusing to wear a head-and-neck restraint. These incidents led to fines, probation, and a reputation as NASCAR's "bad boy."

2001: Cover of NASCAR video game

On March 22, 2007, it was announced that Tony Stewart would be on the cover of the official NASCAR video game, NASCAR 08, published by Electronic Arts. This marked the third time Stewart received this honor (previously in 2001 and 2003).

2002: NASCAR Cup Series Championship as Driver

In 2002, Tony Stewart won his first NASCAR Cup Series championship as a driver.

2002: Winston Cup Championship and Controversies

In 2002, Tony Stewart's Daytona 500 ended early due to a blown engine. He won at Atlanta and Richmond but was involved in a wreck at Darlington, leading to a hospital visit. An altercation with a photographer after the Brickyard 400 resulted in a fine and point deduction. Despite controversies, he won at Watkins Glen and claimed his first Winston Cup championship at the end of the 2002 season.

2002: Won Cup Series Championship

In 2002, while driving for Joe Gibbs, Tony Stewart secured one of his Cup Series championships.

2002: First Cup Championship Comparison

In victory circle on November 20, 2005, Tony Stewart said that he loved winning his 2005 championship better than his 2002 one because his 2005 season was more well-behaved than 2002.

2003: Relatively Incident-Free Season

In 2003, Tony Stewart, as the defending champion, had a relatively incident-free season. He drove a Chevrolet instead of a Pontiac, winning two races at Pocono and Charlotte, and finished seventh in the points standings during the 2003 season.

2003: Cover of NASCAR video game

January 2004: Fourth Place in 24 Hours of Daytona

In January 2004, Tony Stewart teamed with Andy Wallace and Dale Earnhardt Jr. in a Boss Motorsports Chevrolet for the 24 Hours of Daytona. They dominated the race but finished fourth overall and third in the Daytona Prototype class after a suspension issue and a wheel coming off with 15 minutes remaining in the January 2004 race.

November 2004: Ownership of Eldora Speedway

In November 2004, Tony Stewart became the owner of Eldora Speedway, a half-mile dirt track in New Weston, Ohio, known as "Auto Racing's Showcase Since 1954." Stewart began racing there in 1991 and continues to participate in special events.

2004: Altercation with Brian Vickers at Infineon

In 2004 at Infineon, Tony Stewart was spun out by Brian Vickers, leading to a confrontation. Stewart retaliated by throwing a punch through Vickers' window after the race. This resulted in a $50,000 fine, a 25-point deduction, and probation for the rest of 2004.

2004: Second Place Finish in Gatorade 125 and Daytona 500

In 2004, Tony Stewart started the season with a second-place finish in the Gatorade 125. In the Daytona 500, he led 98 laps but ultimately finished second to Dale Earnhardt Jr. That was his best finish in the Daytona 500 in 2004.

2004: Dale Earnhardt Jr.'s Obscenity Fine

On July 29, 2007, Tony Stewart won the Brickyard 400 for the second time. During the victory lane interview, Stewart was penalized 25 points and fined $25,000 for violating NASCAR's policy on the use of obscene language during interviews during the July 29, 2007 race. This was similar to 2004 when Dale Earnhardt Jr. used an obscenity in a post-race interview at Talladega.

November 20, 2005: Second Cup Championship Win

On November 20, 2005, Tony Stewart secured his second Cup Championship. He noted that he valued the 2005 championship more than his 2002 win due to better behavior during the 2005 season. During the 2005 season, Stewart earned a total of $13,578,168, including $6,173,633 for winning the championship.

2005: Second Cup Title and Race Wins

In 2005, Tony Stewart had one of his most successful years, winning his second Cup title. He secured five race wins at Infineon, Daytona, New Hampshire, Watkins Glen, and Indianapolis. This strong performance earned him the No. 1 seed heading into NASCAR's Chase for the Nextel Cup 10-race playoff during the 2005 season.

2005: Second NASCAR Cup Series Championship as Driver

In 2005, Tony Stewart secured his second NASCAR Cup Series championship as a driver.

2005: Won Cup Series Championship

In 2005, while driving for Joe Gibbs, Tony Stewart secured one of his Cup Series championships.

2006: Rookie Record

In 2006, Denny Hamlin finished 3rd, being the highest points finish by a rookie in the modern era besides Tony Stewart.

2006: Worst Cup Season and Chase Miss

In 2006, Tony Stewart experienced his worst Cup season up to that point, finishing 11th in points and missing the Chase for the Nextel Cup. Despite this, he won three races in the 2006 Chase.

2006: Missed Cut for the Chase for the Nextel Cup

In 2006, Tony Stewart missed the cut to qualify for the Chase for the Nextel Cup by 16 points. He finished poorly at Richmond, being displaced in the top ten by Kasey Kahne. He finished the 2006 season 11th in points, but won three races in the Chase later in the year.

2006: Competitive Cars and Shoulder Injury

In 2006, Tony Stewart's season was marked by both highs and lows. He had competitive cars and secured early wins at Daytona and Martinsville. However, he also faced bad luck and suffered a shoulder injury during the Memorial Day Weekend races at Charlotte. He was later substituted by Ricky Rudd during the Dover race and had to drive in pain for several weeks during the 2006 season.

2006: Jimmie Johnson's Championships

On November 20, 2005, Stewart won his second Cup Championship, joining Jeff Gordon as the only active, full-time drivers at the time to have won multiple championships. Jimmie Johnson afterward did so from 2006 to 2010.

March 22, 2007: Cover of NASCAR 08 Video Game

June 4, 2007: Altercation with Kurt Busch at Dover

On June 4, 2007, at the Autism Speaks 400 at Dover, Tony Stewart and Kurt Busch were involved in another altercation. Kurt Busch passed Stewart and made contact, sending Stewart into the wall. During the caution, Busch gave Stewart a profane gesture, leading to a $100k fine for Busch from NASCAR. Stewart received a pre-race warning from NASCAR.

July 15, 2007: Win at USG Sheetrock 400 at Joliet

On July 15, 2007, Tony Stewart led a race-high 108 laps and secured his 30th career NEXTEL Cup win at the USG Sheetrock 400 at Joliet.

July 29, 2007: Second Brickyard 400 Win and Obscenity Fine

On July 29, 2007, Tony Stewart won the Brickyard 400 for the second time. During the race, Stewart made the winning pass by accidentally bending the rear of Kevin Harvick's car. In the victory lane interview, Stewart was penalized 25 points and fined $25,000 for violating NASCAR's policy on the use of obscene language during interviews during the July 29, 2007 race.

August 12, 2007: Win at Watkins Glen

On August 12, 2007, Tony Stewart won the Centurion Boats at the Glen at Watkins Glen after Jeff Gordon spun his car with two laps to go. Carl Edwards challenged Stewart on the final lap but spun out, sealing Stewart's win.

2007: IROC Championship and Offer to Eldora Speedway

In 2007, Tony Stewart participated in the 30th season of IROC, winning two races and the series championship, earning a million dollars. He offered to return his prize money if IROC held an event at Eldora Speedway. Additionally, Stewart's three wins in the Chase races tied him for second-most in Nextel Cup during the 2007 season.

2007: Chili Bowl Nationals and Daytona Speedweeks Wins

In 2007, Tony Stewart started the season by winning his second Chili Bowl Nationals midget car feature. He also won the Budweiser Shootout, his third win in the race, and his qualifying race for the Daytona 500 during the 2007 season.

2007: Chevrolet Sponsorship for Racing Cars

Since 2007, Tony Stewart owns various open-wheel short-track racing cars, many of which are sponsored by Chevrolet. He also owns and drives dirt super late models.

July 5, 2008: Stewart's Illness during Coke Zero 400

On July 5, 2008, during the Coke Zero 400 at Daytona, Tony Stewart felt unwell and handed his car over to former Joe Gibbs Racing teammate J. J. Yeley. Yeley finished the race in 20th place after being involved in two wrecks in the last 5 laps.

July 8, 2008: Stewart Released from Joe Gibbs Racing, Joins Haas CNC Racing

On July 8, 2008, Tony Stewart was released from his contract with Joe Gibbs Racing, due to JGR switching from Chevrolet to Toyota. Stewart was loyal to Chevrolet. Stewart announced his move to Haas CNC Racing to drive a Haas Chevrolet, sponsored by Office Depot and Old Spice. He also acquired half ownership of the team, renamed Stewart-Haas Racing, and became the highest-paid NASCAR driver.

July 2008: Stewart forms Stewart-Haas Racing Partnership

In July 2008, Tony Stewart agreed to partner with Gene Haas in a co-ownership arrangement, forming the Stewart-Haas Racing organization for the 2009 season, marking his departure from Joe Gibbs Racing. Ryan Newman also attended the meeting to finalize his deal with SHR.

August 15, 2008: Ryan Newman signs with Stewart-Haas Racing

On August 15, 2008, Ryan Newman, also from Indiana, signed a multi-year contract to join Stewart-Haas Racing, initially designated as No. 4 but changed to his USAC No. 39. The U.S. Army became the sponsor, relocating from Earnhardt Ganassi Racing.

October 5, 2008: Stewart wins AMP Energy 500 at Talladega

On October 5, 2008, Tony Stewart, driving for Subway, secured his first and only win of the season at the AMP Energy 500 at Talladega. This marked his final victory with Joe Gibbs Racing. Although Regan Smith initially crossed the finish line first, NASCAR penalized Smith for an illegal pass, awarding the win to Stewart.

2008: Tire Issue at Coca-Cola 600

During the 2008 Coca-Cola 600, with only three laps remaining, Tony Stewart experienced a tire issue but managed to prevent a collision with the wall. Due to this, Stewart had to relinquish his lead to Kasey Kahne for a pit stop.

2008: End of time driving No. 20 Joe Gibbs Racing Car

In 2008, Tony Stewart stopped driving the No. 20 Joe Gibbs Racing car, concluding his time with the team.

2008: Third-Place Finish in Daytona 500

In 2008, with Joe Gibbs Racing switching to Toyota, Tony Stewart started the season with a 6th-place start in the Daytona 500. He finished 3rd after being passed by Ryan Newman and Kurt Busch on the last lap of the 2008 race.

June 7, 2009: Stewart Wins Pocono 500

On June 7, 2009, Tony Stewart achieved his first points race win as a driver/owner at Pocono in the Pocono 500, marking the first owner-driver victory in the Cup series since Ricky Rudd in 1998. Stewart also won the Coke Zero 400 at Daytona after a controversial finish by wrecking Kyle Busch.

October 5, 2009: Stewart wins Price Chopper 400

On October 5, 2009, Tony Stewart secured a victory at the Price Chopper 400, subsequently advancing to fourth place in the standings. He concluded the season in sixth position overall.

2009: Fence Climbing and Sponsor Promotions

Following his win in the Pepsi 400, Tony Stewart began climbing the fence after each victory, inspired by Hélio Castroneves. After the 2009 All-Star race, he joked about being too heavy to climb and bought exercise equipment. The Home Depot, a sponsor, capitalized on his success with promotions, offering discounts on ladders, fencing, and bricks.

April 16, 2010: Stewart Wins Pole Position at Texas Motor Speedway

On April 16, 2010, Tony Stewart achieved his first Sprint Cup pole position in five years at Texas Motor Speedway, with a lap speed of 191.327 mph. This race marked Stewart's 400th in the Sprint Cup and his first pole start since October 2005 at Martinsville Speedway.

May 9, 2010: Old Spice Ends Sponsorship with Stewart

On May 9, 2010, reports surfaced that Old Spice would discontinue its sponsorship of Tony Stewart after an 11-year partnership.

September 5, 2010: Stewart Wins Emory Healthcare 500 at Atlanta Motor Speedway

On September 5, 2010, Tony Stewart won the Emory Healthcare 500 at Atlanta Motor Speedway.

October 10, 2010: Stewart Wins Pepsi Max 400 at Auto Club Speedway

On October 10, 2010, Tony Stewart secured a win at the Pepsi Max 400 held at Auto Club Speedway.

October 12, 2010: Mobil 1 Announces Sponsorship Deal with Stewart-Haas Racing

On October 12, 2010, Mobil 1 revealed a sponsorship arrangement with Stewart-Haas Racing to support Tony Stewart's car, starting in 2011. Mobil 1 would serve as the primary sponsor for 11 races, while Office Depot would continue as the primary sponsor for the remaining races of the season. Additionally, Mobil 1 would sponsor Stewart in the Budweiser Shootout and the All-Star Race.

2010: Jimmie Johnson's Championships

June 2011: Stewart and Vickers Involved in Retaliatory Crashes

In June 2011, at Infineon Raceway, Tony Stewart intentionally crashed into Brian Vickers, leading to Vickers retaliating by wrecking Stewart as payback. Stewart admitted to dumping Vickers first due to blocking.

July 27, 2011: First World of Outlaws Win

On July 27, 2011, Tony Stewart achieved his first-ever World of Outlaws race win at Ohsweken Speedway.

October 30, 2011: Stewart Wins Tums Fast Relief 500

On October 30, 2011, at Martinsville Speedway, Tony Stewart secured victory in the Tums Fast Relief 500, leading three times for 14 laps. This win propelled him into championship contention, placing him second in the points standings.

November 20, 2011: Stewart Wins NASCAR Sprint Cup Series Championship

On November 20, 2011, Tony Stewart clinched the NASCAR Sprint Cup Series championship by winning the final race at Homestead-Miami Speedway, with Carl Edwards finishing second. Stewart and Edwards tied on total points, but Stewart won the tiebreaker with five race wins during the Chase. He became the first driver/owner to win the championship since Alan Kulwicki in 1992.

2011: First Owner-Driver Since Alan Kulwicki to win Cup Series Championship

In 2011, Tony Stewart became the first owner-driver since Alan Kulwicki to win the Cup Series championship.

2011: NASCAR Cup Series Championship as Owner/Driver

In 2011, Tony Stewart won the NASCAR Cup Series championship as an owner and driver.

February 11, 2012: Stewart's Finish at Budweiser Shootout

On February 11, 2012, Tony Stewart led the final stages of the Budweiser Shootout, passing Marcos Ambrose on the last lap. However, he was overtaken by Kyle Busch in a close finish. Stewart also won the 1st duel of the Gatorade Duels at Daytona, where Danica Patrick crashed on the final lap.

March 25, 2012: Stewart wins rain-shortened Auto Club 400

On March 25, 2012, Tony Stewart won the rain-shortened Auto Club 400 at Auto Club Speedway.

June 3, 2012: Stewart involved in 13-car crash at Dover

On June 3, 2012, Tony Stewart was involved in a 13-car crash on the back leg at Dover, finishing the race in 25th place.

October 2, 2012: Bass Pro Shops to Sponsor Stewart in 2013

On October 2, 2012, it was announced that Bass Pro Shops would serve as a co-primary sponsor for Tony Stewart in a selection of races during the 2013 season.

2012: Chase for the Sprint Cup

After winning at Sonoma in 2016, Stewart became part of the Chase for the first time since 2012.

2012: Stewart's Incident with Kenseth at Bristol

During the 2012 Irwin Tools Night Race at Bristol, Tony Stewart and Matt Kenseth tangled while battling for the lead on lap 333, resulting in a caution. After exiting his wrecked car, Stewart threw his helmet at Kenseth's car and gestured applause to the fans. This was followed by Danica Patrick wagging a finger at Regan Smith after he turned her into the wall.

2012: Stewart's Comments on Earnhardt Jr.'s Win

In 2012, Tony Stewart led 18 laps at the Quicken Loans 400 and finished second. However, he faced criticism for stating that Dale Earnhardt Jr.'s win "Is not a national holiday," taunting the Earnhardt nation for celebrating the fourth anniversary of Earnhardt's last win in 2008.

August 11, 2013: Max Papis to fill in for Stewart

On August 11, 2013, it was announced that Max Papis would fill in for Tony Stewart at Watkins Glen International, due to Stewart's leg injury.

August 19, 2013: Stewart Ruled Out for Remainder of Season

On August 19, 2013, Tony Stewart was ruled out for the remainder of the season due to the leg injury he sustained, and Mark Martin was signed to drive Stewart's car for the remaining races.

2013: Nationwide Series Win at Daytona and Daytona 500 Crash

In 2013, Tony Stewart won the Nationwide Series event at Daytona, but his win was overshadowed by a crash involving Kyle Larson and injuring spectators. He also crashed early in the Daytona 500, finishing 41st.

2013: Sole Sprint Cup Win of 2013

In 2013, at Dover, Tony Stewart secured his sole Sprint Cup win of the year after overtaking Juan Pablo Montoya in the last laps. This victory propelled him to 16th position, earning him a Wildcard spot and marking his 15th consecutive season with at least one race win.

February 15, 2014: Return to Sprint Car Racing

On February 15, 2014, Tony Stewart made his return to sprint car racing, driving the same No. 14 car in which he broke his leg in 2013, and silenced critics with a dominant win at Tri-City Motor Speedway.

August 15, 2014: NASCAR Rule Change After Ward's Death

On August 15, 2014, NASCAR announced a rule change, following the death of Kevin Ward Jr., mandating that drivers involved in accidents must remain in their vehicles until emergency crews arrive, unless there is an emergency.

August 17, 2014: Jeff Burton Replaces Stewart

For the August 17, 2014, race at Michigan, Jeff Burton replaced Tony Stewart, who also missed the following race at Bristol, but returned at Atlanta and received a waiver for Chase eligibility.

October 7, 2014: Three Career World of Outlaws Main Event Victories

By October 7, 2014, Tony Stewart had accumulated three career World of Outlaws main event victories, competing with various Sprint Car series.

2014: NASCAR Cup Series Championship as Owner

In 2014, Tony Stewart achieved a NASCAR Cup Series championship as a team owner.

2014: Worst Statistical Year as a Driver

In 2014, Tony Stewart had his worst statistical year as a driver, ending his 15-year winning streak with a last-place finish at Homestead-Miami; however, he won the Owner's Championship with Kevin Harvick.

September 27, 2015: Retirement Plans Reported

On September 27, 2015, it was reported that Tony Stewart announced his plans to retire from racing after the 2016 season.

September 30, 2015: Retirement Officially Announced

On September 30, 2015, Tony Stewart formally announced his retirement after the 2016 season, confirming that Clint Bowyer would replace him in the No. 14 car in 2017.

2015: Crash at the CampingWorld.com 500

During the 2015 CampingWorld.com 500, Tony Stewart, after qualifying 17th, crashed on lap 288, resulting in a caution, while his teammate Kevin Harvick went on to win the race.

2015: Difficult 2015 Season

In 2015, Tony Stewart faced a challenging season, failing to secure a win for the second consecutive year and missing the Chase, despite qualifying well in several races. He only scored 3 top-10 finishes.

April 24, 2016: Return to Racing at Richmond

On April 24, 2016, Tony Stewart returned to racing at the Toyota Owners 400 at Richmond, finishing 19th, after missing the first eight races of the season due to a back injury.

2016: Last Full-Time Season in NASCAR Sprint Cup Series

In 2016, Tony Stewart last competed full-time in the NASCAR Sprint Cup Series, driving the No. 14 Chevrolet SS for Stewart-Haas Racing.

2016: Controversy at Richmond and Final Race

In 2016, at Richmond, Tony Stewart was involved in a controversy after wrecking Ryan Newman. His bid for a fourth title ended after poor finishes. He wrapped up his 18-year career with a 22nd-place finish at the 2016 Ford EcoBoost 400.

2016: Retirement Confirmed

In September 30, 2015, Tony Stewart confirmed his retirement after the 2016 season.

2017: Clint Bowyer to Replace Stewart

In September 30, 2015, Tony Stewart announced that Clint Bowyer would replace him in the No. 14 car in 2017.

2020: Xfinity Series Return Cancelled

In 2020, Tony Stewart's planned return to the Xfinity Series for the Pennzoil 150 was cancelled due to the COVID-19 pandemic.

2021: SRX Series Championship Win

In 2021, Tony Stewart won the Superstar Racing Experience (SRX) Series championship after securing a podium finish in the inaugural race and sweeping the dirt track races, ultimately winning by 45 points.