12 Underdog Wins That Shocked the NASCAR World
These unforgettable NASCAR upsets prove that grit, luck, and perfect timing can sometimes beat the biggest names on racing’s grandest stages.
- Alyana Aguja
- 5 min read
NASCAR have always celebrated speed and ability, yet it’s those upsets of underdog drivers and small organizations that really show the heart of the sport. Last-lap miracles and strategy plays in rain, these stunners by dark-horse drivers and small-time organizations defied odds and sent shockwaves into the foundations of racing giants. Each story serves as a reminder that with NASCAR, anything can happen, and sometimes it happens in the grandest fashion.
1. Trevor Bayne – 2011 Daytona 500
Image from Wikipedia
In his second Cup Series start and at just 20 years of age, Trevor Bayne stunned the world by taking the 2011 Daytona 500 for Wood Brothers Racing. The historic team had not won a race since 2001 or the Daytona 500 since 1976. Bayne beat back a hard-charging group of veterans, making his name in NASCAR history.
2. Michael McDowell – 2021 Daytona 500
Image from ESPN
Finally, after 357 starts without a win, journeyman Michael McDowell led a triumphant Front Row Motorsports across the finish line at the 2021 Daytona 500. In a tense battle, he drove past for the checkered flag, staying just ahead of a blazing last-lap wreck. The financially struggling team commemorated one of the most improbable wins in NASCAR’s recent past.
3. Ward Burton – 2002 Daytona 500
Image from Wikipedia
Ward Burton was not thought of as a favorite going into the 2002 Daytona 500, but he took advantage of a crazy race to score the victory. Behind the wheel for Bill Davis Racing, a middle-of-the-pack team, he survived a crash-filled day to win his largest career victory. It was a tearful victory that caught fans and experts off guard.
4. David Ragan – 2013 Aaron’s 499 (Talladega)
Image from Wikipedia
David Ragan provided Front Row Motorsports with its inaugural Cup Series victory at Talladega in 2013. He pulled off a flawless last-lap pass on teammate David Gilliland to take the win away from juggernaut teams. The 1-2 result was one of the biggest surprises in NASCAR’s restrictor-plate era.
5. Chris Buescher – 2016 Pocono 400
Image from RFK Racing
Chris Buescher and the small Front Row Motorsports team sneaked into the victory lane in 2016 at Pocono, following a timely caution and thick fog. NASCAR deemed the race official with 22 laps left, closing the deal for the rookie. A heads-up game plan play earned Buescher his first—and completely shocking—Cup victory.
6. Justin Haley – 2019 Coke Zero Sugar 400 (Daytona)
Image from NASCAR.com
In just his third Cup Series appearance, Justin Haley pulled off an astonishing victory in a rain-cut short Daytona event. Competing for Spire Motorsports, a team with little or no previous success, he led on the track while others stopped for pit cycles and went first when weather conditions brought the event to a close. It was one of the most unlikely victories in Cup Series history.
7. Derrike Cope – 1990 Daytona 500
Wikipedia
Derrike Cope’s win at the 1990 Daytona 500 is still one of the best-known upsets in NASCAR. Dale Earnhardt was in front on the last lap when he blew a tire, which opened the way for Cope to speed ahead to victory. No one could have predicted it—particularly from a driver with no wins and few top finishes.
8. Ron Bouchard – 1981 Talladega 500
Image from Wikipedia
Ron Bouchard made a miracle three-wide pass on the last lap to take the 1981 Talladega 500. The rookie edged legends Darrell Waltrip and Terry Labonte in a photo finish that amazed the field. It was his sole career victory and is still the subject of conversation decades later.
9. Lake Speed – 1988 TranSouth 500 (Darlington)
Image from eKartingNews
With a shoestring budget and his own team, Lake Speed dominated Darlington in 1988 for his lone Cup win. He led 178 of 367 laps in a surprising performance no one could have predicted. The win came against all odds and showed that sometimes, heart beats horsepower.
10. Regan Smith – 2011 Southern 500 (Darlington)
Image from Wikipedia
Racing for underdog Furniture Row Racing, Regan Smith stunned the NASCAR world by capturing the coveted Southern 500 in 2011. He edged Carl Edwards in a thrilling finish, holding on through restarts and mayhem. It was a milestone win for both Smith and the single-car Denver-based team, remote from NASCAR’s Charlotte headquarters.
11. Trevor Bayne – 2011 Nationwide Series Win at Texas
Image from ESPN
Earlier the same year that he won the Daytona 500, Bayne won his first NASCAR Nationwide Series race at Texas, driving for Roush Fenway Racing. While Roush was a large team, Bayne was still an underdog among veterans and up-and-comers. His cool driving and clutch performance were indications that great things were on the horizon.
12. Bobby Hillin Jr. – 1986 Talladega 500
Image from Toolbox Ministries
At 22, Bobby Hillin Jr. was the youngest Talladega winner in 1986 when he drove for Stavola Brothers Racing. He took advantage of late-race attrition and timed his moves to perfection to get to the front. The victory was the sole one of his career and a shocker in an era of big-name domination.