Top 15 Biggest Upsets in NASCAR History

15. Bobby Hillin Jr. Wins at Talladega – 1986

At just 22 years old, Hillin became the youngest driver to win a Cup race at the time—his only career win.

14. AJ Allmendinger Wins at Indianapolis – 2021

In a chaotic road course debut at Indy, Allmendinger came from nowhere to give Kaulig Racing its first-ever Cup Series win.

13. Phil Parsons Wins at Talladega – 1988

Parsons, not a usual front-runner, led a RCR 1-2 finish in a wild superspeedway race. It was special time for RCR, as the legendary team was still in its building phase.

12. Trevor Bayne’s Dual Win Over Jimmie Johnson – 2011

Before his Daytona 500 win, Bayne shocked everyone by going toe-to-toe with a five-time champion in a qualifying race.

11. Brad Keselowski Wins at Talladega – 2009

In just his fifth Cup start, Keselowski held off Carl Edwards (who crashed over the finish line) to earn a dramatic first win. It started the Hall of Fame worthy legacy of the 2012 Cup champion.

10. Jeremy Clements Wins Xfinity at Road America – 2017

Driving for his family-owned team, Clements made a bold last-lap move and won—an underdog fairytale in the modern era.

9. Ron Bouchard Wins at Talladega – 1981

In a three-wide finish, Bouchard shocked the NASCAR world by beating Darrell Waltrip and Terry Labonte in a photo finish.

8. Regan Smith Wins at Darlington – 2011

Smith held off Carl Edwards at one of the toughest tracks in NASCAR, earning Furniture Row Racing its first win ever, starting a short era of domination for the team.

7. Derrike Cope Wins the 1990 Daytona 500

After Dale Earnhardt cut a tire on the final lap, Cope snuck by and captured a historic and unexpected win. Stealing the win from The Intimidator, that’s something.

6. Justin Haley Wins at Daytona – 2019

Driving for Spire Motorsports, which was a new and small team then, Haley stayed out during a caution and was declared the winner after lightning and rain ended the race early. The win also helped him to impress the love of his life, so another big win.

5. Chris Buescher Wins at Pocono – 2016

Fog shortened the race, and a timely strategy helped Buescher and FRM steal an unlikely win, marking another upset win in the Bob Jenkins’s team’s history

4. Ward Burton Wins the 2002 Daytona 500

Not many expected Burton, a mid-tier driver at the time, to capture NASCAR’s biggest prize. But Daytona gives driver willing take risks a chance and he took it with both hands.

3. David Ragan Wins at Daytona – 2013

Driving for underdog FRM, when Ragan pulled off a surprise win in a wild race—against the top teams in the sport at Daytona, the whole garage was speechless.

2. Michael McDowell Wins the 2021 Daytona 500

A driver who has been a journey man for the lower table side, winless for over 350 races winning Daytona 500, now that’s special. After 358 starts without a win, McDowell avoided a last-lap wreck and shocked the world with a victory for Front Row Motorsports.

1. Trevor Bayne Wins the 2011 Daytona 500

Okay a 20-year-old driving part-time driver for Wood Brothers Racing winning the biggest race of the season, now that’s an upset. That exactly what Trevor Bayne did in 2011, as he stunned the field and became the youngest Daytona 500 winner—in just his second Cup start.