Small Names, Massive Victory Moments
Nobody sees them coming and that’s the beauty of it. Sometimes a race ends and the garage freezes, asking, “Wait… who?” These surprise wins rattled the sport. While most think “NASCAR history” means Cup races, a few Xfinity and Truck upsets made the cut, for how deeply they shook the system. Here are the top 20 upsets in NASCAR history.
1. Trevor Bayne: Daytona 500 (2011)
Trevor Bayne stunned the motorsports world by bagging the Daytona 500 in his second Cup start. At 20, he displayed rare composure while piloting an underdog Wood Brothers Ford. That day, youth outpaced experience, and a legacy was born amid roaring disbelief.
Chris Short from Detroit, MI, United States on Wikimedia
2. Derrike Cope: Daytona 500 (1990)
When Dale Earnhardt blew a tire on the last lap, Derrike Cope didn’t hesitate. He seized victory in a jaw-dropping moment few saw coming. From obscurity to center stage, Cope's name became permanently etched into the annals of Daytona lore.
3. Michael McDowell: Daytona 500 (2021)
After 358 starts without a win, Michael McDowell delivered in NASCAR’s biggest race. He avoided chaos in the final lap, crossing the line as a first-time victor. For Front Row Motorsports, it was a storybook ending no scriptwriter could’ve topped.
Zach Catanzareti Photo on Wikimedia
4. Ward Burton: Daytona 500 (2002)
Ward Burton claimed an unlikely Daytona 500 win amid a chaotic, crash-heavy race. Driving for Bill Davis Racing, he stayed clean when it counted. The victory was both strategic and symbolic, and it put a quiet grinder atop the sport’s biggest podium.
5. David Ragan: Daytona (July 2011)
This driver rebounded from heartbreak earlier that year by triumphing in July’s Daytona race. He executed flawless strategy and timing, erasing past missteps. His win felt like poetic justice at a track where redemption stories are often hard-earned.
David Ragan wins Coke Zero 400 at Daytona in July 2011 by NASCAR
6. Chris Buescher: Pocono (2016)
Rain and fog changed everything, but Chris Buescher kept himself in a position to capitalize. Driving for Front Row Motorsports, he took a surprise win that baffled experts. This race was a show of his patience and track sense, which turned an ordinary run into a career-defining moment.
Recap: Buescher's breakthrough win at Pocono by NASCAR
7. Regan Smith: Darlington (2011)
Regan Smith beat NASCAR’s elite at the notoriously brutal Darlington Raceway. Here, he held off Carl Edwards with grit, smarts, and perfect execution. For Furniture Row Racing, it was their first Cup win, delivered at one of the hardest tracks to tame.
8. Justin Haley: Daytona (July 2019)
In only his third Cup start, Justin Haley stunned the field with a rain-shortened Daytona win. Positioned perfectly before the weather halted the race, Haley’s timing was impeccable. It was a Cinderella story delivered during a weekend of pure chaos.
Coke Zero Sugar 400 at Daytona | NASCAR on FOX HIGHLIGHTS by NASCAR on FOX
9. David Gilliland: Talladega (Xfinity, 2006)
David Gilliland bested a field full of Cup regulars at Talladega with pure audacity. Driving for a lesser-known team, he stormed to the front with calculated aggression. It was a shocking breakout moment that jump-started his NASCAR career overnight.
10. Paul Menard: Brickyard 400 (2011)
When Paul Menard triumphed at the legendary Indianapolis Motor Speedway using a crafty fuel strategy, it was legendary. As laps wound down, he conserved just enough to hold off charging contenders. His name joined an elite club at one of racing’s most sacred venues.
11. Brad Keselowski: Talladega (2009)
Brad Keselowski executed a bold last-lap pass at Talladega, colliding with Carl Edwards in a shocking finish. Racing for a small team, he outmaneuvered giants with fearless precision. The crash, the drama, and the underdog victory made it an unforgettable moment in NASCAR history.
12. Bobby Hillin Jr.: Talladega (1986)
At 22, Bobby Hillin Jr. won Talladega by keeping his cool amid veteran chaos. While driving for the Stavola Brothers, he capitalized on late-race mistakes. Here is where his composure and perfect positioning turned him into the youngest superspeedway winner of that time.
13. Aric Almirola: Daytona (July 2014)
In 2014, Aric Almirola delivered Richard Petty Motorsports a symbolic victory at Daytona on the July 4th weekend. Rain shortened the race, but he had already surged to the lead. This win revived the legendary No. 43 car’s presence on the sport’s biggest stage.
Capt. Brian Wagner on Wikimedia
14. Ron Bouchard: Talladega (1981)
In a legendary three-wide photo finish, Ron Bouchard surged from third to first in the final seconds. With Waltrip and Labonte battling, Bouchard seized his moment. His perfectly timed move stunned fans and remains one of Talladega’s most iconic victories.
Ron Bouchard's 1981 Talladega Winning Race Car ON DISPLAY! by Ron Bouchard
15. Phil Parsons: Talladega (1988)
Phil Parsons led over 50 laps and dominated Talladega in a breakout performance. He drove with unmatched confidence for a lesser-known team and left the field chasing shadows. This, as his only Cup win, came through control, not chaos, and that’s a rare thing at that track.
16. Lake Speed: Darlington (1988)
Lake Speed’s lone Cup victory came at the unforgiving Darlington Raceway, where he outran NASCAR legends. Operating a self-owned car, he executed a flawless drive under intense pressure. His win represented individual determination to overcome the sport’s toughest challenge.
The Scene Vault Podcast -- Lake Speed's 1988 Darlington Raceway Win by The Scene Vault
17. John King: Daytona (Truck Series, 2012)
Rookie John King stunned the Truck Series world by winning Daytona in his first full-time season. He maneuvered through carnage and took the lead with bold moves late. King’s name shot from unknown to unforgettable with one perfectly timed finish.
Victory Lane: John King by NASCAR
18. Trevor Bayne: Texas (Xfinity, 2023)
Years after his Daytona heroics, Trevor Bayne returned to Xfinity and claimed a win at Texas. With limited seat time, he showed racecraft that surprised even seasoned fans. This comeback highlighted persistence and readiness, meeting opportunities at full throttle.
Trevor Bayne Finished 3rd At Auto Club in Xfinity Return "I Expected a Win" by Frontstretch
19. Jeremy Clements: Road America (Xfinity, 2017)
Driving for his family-run team, Jeremy Clements beat the odds at Road America with a gutsy late-race pass. Against powerhouse teams, he drove with fearless purpose. That daring move carved him a spot in NASCAR’s most inspiring upsets.
Exhilarating Moments: Jeremy Clements spins, wins first XFINITY race by NASCAR
20. Cole Custer: Kentucky (2020)
Cole Custer rocketed from fourth to first in a final-lap dash at Kentucky. His outside move against veteran contenders defied logic—and delivered results. It was a thrilling, aggressive push from a rookie who refused to wait his turn.
Recap: Cole Custer scores first career NASCAR Cup Series win at Kentucky Speedway by NASCAR
