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5 Most Important Moments of Tony Stewart’s NASCAR Career

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Now that it is official that his NASCAR career is coming to a close after 25 seasons, we here at the Daily Downforce thought it would be a fun idea to look back at some of Smoke’s biggest and most important moments.

Despite your opinions on Stewart’s waning interest in NASCAR (and what you pin your blame on) it cannot be denied that Tony Stewart is one of – if not the – most talented drivers to ever sit inside a NASCAR stock car. He can (and has) won in any and everything from Indycar, to NASCAR, to the World of Outlaws, to IROC, to SRX, to even the NHRA.

But for most fans of motorsports, Tony Stewart is best known for his time as a NASCAR driver, which he was from 1999-2016. He also served as an owner of Stewart-Haas Racing from 2017-2024.

With no further ado, here are the 5 Most Important Moments of Tony Stewart’s NASCAR Career.

#1: Stewart’s First NASCAR Win

By the time Tony Stewart entered the NASCAR Cup Series in 1999 as a rookie, he was already a successful professional racecar driver. He was a 3-time winner of the Indy Racing League (a predecessor to the modern-day unified IndyCar), and he won the series championship in 1997. But perhaps seeing the writing on the wall when it came to American open-wheel racing and considering the infamous fractured split that lasted until 2008, Stewart decided to make the jump over to NASCAR, which was growing in popularity

In 1998, Tony Stewart ran most of the Busch Series schedule that season, driving a number 44 Pontiac for Joe Gibbs Racing. This was in preparation for his full-time run with the team’s Cup Series program in 1999. Throughout the early parts of the 1999 Cup Series season, Stewart had some promising finishes inside the top 5 and top 10, but it was at the 25th race of the season at Richmond International Raceway that his immense potential would finally be fulfilled.

In the fall Richmond race of ’99, Tony Stewart impressed in qualifying as he captured his 5th front row start of the season. Tony Stewart took the lead from Mike Skinner on the second lap and never really looked back. He ended up leading 333 laps of the race’s 400, showing his dominance. It was the first win of Tony Stewart’s NASCAR career and one that kicked off a truly legendary career in the sport. You can relive the race in its entirety in the video below.

#2: Stewart’s First Cup Series Championship

By the time the 2002 NASCAR Cup Series season came around, Tony Stewart was starting to make a name for himself in the top tier of NASCAR. In 2000, he had 6 total wins and ended up finishing 6th in the Cup Series standings. So he knew how to find victory lane, he just needed to home in on his consistency. He did just that in 2001 by capturing 3 wins but running consistently enough to finish 2nd in the overall point standings to series champion Jeff Gordon.

In 2002, it was time for Stewart to take that next step from championship contender to championship favorite, and he did just that. This season, he matched his win total of 3 from the previous year and put up similar numbers. However, early on in the season, it seemed to be more of the same. Inconsistency plagued the No. 20 Home Depot team from the jump in 2002. However, as the season ramped up and talks about a championship took a serious turn, they were able to run a little more consistently.

As the year came to a close, Stewart was a consistent top-5 and top-10 runner, which, along with his three wins at Atlanta, Richmond, and Watkins Glen that season, helped him edge out Mark Martin for the 2002 NASCAR Winston Cup Series Championship.

#3: Becoming the Only Driver (So Far) To Successfully Complete “The Double” (2001)

This Memorial Day weekend, a lot of eyes were on Kyle Larson as he attempted what nobody had since Kurt Busch did it in 2014–The Indy 500/Coke 600 Double. But long before either of those attempts, Tony Stewart attempted the infamous “Double” on two occasions. He first attempted it in 1999 but was unable to complete all 1,100 miles of racing. However, in 2001 Tony Stewart went on to do the unthinkable: not only did he attempt The Double, he COMPLETED it, racing and finishing on the lead lap in all 1,100 miles.

At Indy, after a rain delay during which he was leading the race, Tony Stewart went on to finish 6th. That night in Charlotte, he went on to finish 3rd. Maybe someday Kyle Larson will get to become the second driver in history to complete the Indy500/Coke 600 Double but as of 2024, Stewart stands alone as the only driver to claim this crowning achievement.

#4: Stewart Championship Win as an Owner/Driver (2011)

When Tony Stewart left Joe Gibbs Racing (where he already had won 2 Cup Series titles) for a struggling Haas CNC Racing to form the rebranded Stewart-Haas Racing, many considered it career suicide. Think about it: in 2008, Kyle Busch arrived at JGR and went on a complete tear. They were winning races left and right, and it seemed that KFB was there to elevate the organization as a whole. But with this move, Smoke was no longer the top dog on the team. Also, since he still had ties with Chevrolet in his dirt racing team, the timing was perfect for Stewart to make some big career moves.

At the time, Hendrick Motorsports’ number 5 car was up for grabs, and while it appeared that Brad Keselowski was in prime position to take over the ride, considering his resume, Smoke had to be among the front runners for the ride. Mr. H proved with the signing of Mark Martin that he wasn’t resistant to signing a seasoned veteran to drive the team’s flagship number 5. So why did Stewart skip out on HMS to join Gene Haas and form Stewart-Haas Racing? Stewart had spent the first 10 years of his career driving for someone else. Maybe he thought by 2008 that he was in a position in his career than to start calling some of the shots himself.

Tony Stewart’s involvement in Stewart-Haas Racing elevated a struggling team to a team that was contending for races week in and week out. In 2009 (Stewart’s first year as an owner/driver), was a successful year with Stewart winning a handful of races for his own team. But two years later, the team really hit their stride.

In the beginning and even halfway through the 2011 season, Smoke’s year appeared to be mediocre at best. As he entered that year’s Chase for the Cup, he had zero wins and infamously spouted that he was “just taking a spot from a more deserving driver.” But in the season’s final stretch, Stewart went on an absolute tear! He went on to win 5 of the final 10 races en route to his third overall driver championship, first as an owner/driver, something nobody had done in NASCAR since Alan Kulwicki’s Championship season in 1992.

#5: Stewart’s Final Cup Win (Sonoma 2016)

Following his 2011 championship, Stewart’s career started to fall off. While it wasn’t an initial nosedive in statistics, the last handful of years in the NASCAR Cup Series had a lot of off-track struggles that overshadowed how he was running on the track. He suffered a lot of injuries in the closing years of his career as well as a tragedy that took him out of the car for several weeks in the 2014 season.

When Smoke announced that 2016 was to be his final year in the sport, many fans were relieved, believing that his time had come and gone as a competitive NASCAR driver. But hopes were high for Stewart in his farewell tour as his colleague, Jeff Gordon, had some of the best retirement tour numbers just the year before. Many fans wondered if they had already seen Stewart’s last win or if he could pull into victory lane one final time in 2016.

Tony Stewart won his final NASCAR Cup Series race on June 26, 2016 and the victory came at one of his most successful tracks–Sonoma Raceway. In the closing laps of the race, Tony Stewart was battling former teammate Denny Hamlin hard. When it looked as if Smoke had squandered the chance at his final win, Stewart roughed up Hamlin in turn 11 as only Tony Stewart can. Stewart crossed the line first and went on to celebrate his final win at NASCAR’s top level.


Well, Daily Downforce fans, what are your all-time favorite Tony Stewart moments? Are you surprised by the closure of Stewart-Haas Racing, or is it one of the things you can see coming from a mile away? Let us know your thoughts and what you think is Tony Stewart’s most impressive achievement as a driver or a car owner by commenting on all our social media platforms. And be sure to keep it right here at for all the latest silly season rumors, news, and fan discussions in the world of NASCAR.

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Cody Williams

Cody Williams is the author of BUNNY BOY and THE FIFTH LINE. He lives near Bristol, TN.
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