The 2007 New York Giants toppling Tom Brady’s run at perfection. The Pittsburgh Pirates upsetting the New York Yankees, by way of Bill Mazeroski’s walk-off home run in Game 7 of the 1960 World Series. There’s nothing like a great underdog story, and even NASCAR is not short of them. With that said, what is the greatest upset in NASCAR history.

Image: Cody Wansley/Seriously Fast Media

Honorable Mentions

Needless to say, this is a very subjective exercise. Your answer may be different than mine. I’ve put to together my list of the greatest upsets in NASCAR history, but first some Honorable Mentions:

Derrike Cope, 1990 Daytona 500: In one of the most iconic endings in NASCAR history, Cope won the 1990 Daytona 500 on a last lap pass. Of course, passing Dale Earnhardt, who suffered a flat tire entering Turn 3.

Jamie McMurray, 2002 UAW-GM Quality 500: McMurray was filling in for an injured Sterling Marlin late the 2002 season. McMurray shocked the sport when he led 96 laps, and held off 2000 Series Champion Bobby Labonte late to win in just his 2nd Start in the Cup Series.

Ricky Craven, 2003 Carolina Dodge Dealers 400: The closest finish in NASCAR Cup Series history (Up until Kansas earlier this season). Craven led just 1 lap in this race, which of course was the most important one. It was Craven’s 2nd and final win of his career.

Paul Menard, 2011 Brickyard 400: There were four remarkable upsets in 2011, this being one of them, two of them made the Top 5 of this list and the third did not make the list. In the 2011 Brickyard 400, Menard survived a dramatic fuel mileage race to collect his one and only win in the Cup Series.

Michael McDowell, 2021 Daytona 500: In one of the most dramatic finishes in the history of the race, McDowell was the first driver through the incident and finally clinched his first career win, and the 2nd win for Front Row Motorsports.

The Top 5 Upsets in NASCAR History

Now on to the Top 5. It’s worth noting that I only considered moments from what NASCAR considers to be the “Modern Era” of NASCAR (1972-Present).

5. Geoffrey Bodine, 1984 Sovran Bank 500

Otherwise known as the race that kickstarted an Auto Racing Empire. The first ever win for Hendrick Motorsports. Though at the time they were known as All-Star Racing. In a race dominated by Bobby Allison, who led 266 laps en route to a 4th place finish, Bodine drove the #5 to Victory Lane in what was likely the teams last chance.

Obviously, we are now very aware of what that win started, with the team that would become Hendrick Motorsports going on to win 14 Championships. Of course, they are in contention with all 4 of their drivers to add to that number this year, the 40th Anniversary of the team and this most incredible upset.

4. Trevor Bayne, 2011 Daytona 500

Bayne entered the 2011 Daytona 500 with one previous start in the Cup Series. The then 19-Year Old made his Cup Series debut at Texas Motor Speedway in the Fall of 2010 in the iconic Woodbrothers #21. Bayne was tapped to drive the legendary car 17 more times in 2011, starting the day after his 20th birthday with the Daytona 500.

He started in 32nd after getting caught in an incident in his Duel on Thursday. Bayne survived a chaotic race with 16 cautions and 2 overtime attempts. He got a little lucky, with David Ragan getting penalized for changing lanes before the Start/Finish Line. And he managed to save enough fuel to hold off Carl Edwards, David Gilliland, and Bobby Labonte en route to his only win in the Cup Series.

3. Harrison Burton, 2024 Coke Zero Sugar 400

Bayne’s historic Daytona 500 win was the 98th for the Woodbrothers Racing team. Ryan Blaney gave them their 99th at Pocono in 2017. Paul Menard and Matt Dibenedetto drove the car for 2 years each after Blaney was promoted to the #12 for Team Penske. Entering the 2022 season, Woodbrothers Racing signed Harrison Burton, son of 21-Time Cup Series Winner Jeff Burton, to take over the team’s pursuit of their 100th Win. Burton’s first race in the car proved to be a bad omen for his tenure.

On lap 63 of the 2022 Daytona 500, Burton went airborne and landed on his roof before rolling back onto his wheels. Burton has been largely disappointing, with an average finish of 24.46 in his 3 Years with the team. But in his final race at Daytona in the #21, Burton was one of few to survive the chaos of the 2024 Coke Zero Sugar 400. His future replacement, Josh Berry, flipped wildly down the backstretch, from the lead with just 2 Laps To Go. Burton took the outside of the front row, alongside Kyle Busch, on the Final Restart and he made the most of it.

With some…controversial…help from Parker Retzlaff, Burton powered by the incumbent Kyle Busch into Turn 3 on the Final Lap. With an aggressive block coming to the Start/Finish Line, Burton clinched his First Career Win. Burton ends a tumultuous tenure at Woodbrothers Racing after the Season Finale at Phoenix, in November. Where Burton goes from there is unknown at the moment. But despite all of the struggle, he gets to go out on the highest of highs.

2. Regan Smith, 2011 Showtime Southern 500

In 2008, Regan Smith was driving for Dale Earnhardt Inc. in the #01 car. In that years Fall Talladega race, Smith was 2nd coming to the Checkered Flag when he made his move on Leader Tony Stewart. Smith faked high, Stewart blocked. Smith ducked low, Stewart attempted a block, but Smith had gotten his nose to Stewart’s quarter panel. Stewart blocked anyway, they made slight contact and Smith went below the yellow line so as to not wreck Stewart.

Smith made the pass for the win and crossed the line first. However, NASCAR penalized Smith. This penalty is directly responsible for the incident on the Final Lap of 2009’s Spring Talladega race. In which Carl Edwards went airborne after Brad Keselowski refused to go below the line to avoid contact, so that he would avoid a penalty.

It was a beautiful May Night in South Carolina, and the heartbreak from that day had subsided. Smith had moved on from DEI. To a small team that operated out of Denver, Colorado, of all places. Furniture Row Racing. Smith would roll off in 23rd for the 2011 Edition of the Southern 500. Ut was a night of chaos and carnage that was dominated by Pole sitter Kasey Kahne. With 4 Laps To Go, Kyle Busch, Kevin Harvick and Clint Bowyer were 3-Wide coming off of Turn 4. Bowyer would get the short end of the stick and be sent to the inside wall. Busch promptly turned Harvick after the Caution came out.

Smith’s Crew Chief, Pete Rondeau, made an incredibly ambitious call to keep Smith out on old tires. With Carl Edwards and Brad Keselowski in 2nd and 3rd, respectively. It seemed that they had Smith dead to rights. But Smith got a good launch on the overtime restart and cleared Edwards into Turn 1.

Smith took the White Flag with a 2 and a half car length lead over Edwards. Off Turn 2, both drivers would tag the wall, preventing Edwards from getting a run. Smith would hold off Edwards through 3 & 4 and took the Checkered Flag. And this time, he got to keep it.

1. Alan Kulwicki, 1992 Season

The Greatest Underdog…or Under-“bird” rather, in NASCAR history. In what many consider to be NASCAR’s Greatest Season, Alan Kulwicki beat out both Bill Elliott and Davey Allison for the 1992 Cup Series Title.

In 1987, Kulwicki opened his own race team and entered the season as an Owner/Driver. Despite many growing pains, Kulwicki drove his car to 3 Poles and a 15th Place Points finish. The 1988 season was much of the same, but ended on a high, as Kulwicki captured his first career win at Phoenix.

By 1992, Kulwicki had improved his car to being a genuine title threat. As the season waned, his consistency was remarkable. He had picked up 16 Top-10s and 10 Top-5s through the first 28 races of the season. Heading into the season finale at Atlanta Motor Speedway, Kulwicki trailed Davey Allison by 30 Points. Bill Elliott sat 40 Points back from Allison, and Harry Gant, Kyle Petty and Mark Martin were 4th, 5th, and 6th, all with an outside shot at the title if something went wrong for the Top 3.

Allison would finish 27th and never really be a player, so the focus was on Elliott and Kulwicki. By the end of this race (which featured the final race of Richard Petty’s career and the beginning of debutante, Jeff Gordon’s career)y, the championship would come down to Laps Led. Elliott led 102 Laps while Kulwicki led 103. This was during the time where leading a lap was worth 5 points. You were also given 5 bonus points for leading the Most Laps.

Kulwicki would win the title by 10 Points over Elliott. Had Elliott led an extra lap and Kulwicki one fewer, history would be telling a far different story.