Top 10 Biggest NASCAR Upsets in Daytona 500 History

Biggest Upsets in Daytona 500 History

Michael McDowell – 2021

10. Ryan Newman – 2008

Tony Stewart controlled most of the race, and Newman had not won in years. A final-lap push from Kurt Busch stunned the field and delivered Penske its first Daytona 500 win.

9. Austin Dillon – 2018

Dillon entered the season with little momentum and led only one lap in the race. A last-lap move on Aric Almirola put the No. 3 back in Victory Lane on the sport’s biggest anniversary.

8. Michael Waltrip – 2001

Waltrip had gone winless in 462 starts before joining Dale Earnhardt Inc. His first career win came in the Daytona 500 and stands as one of the most emotional finishes in NASCAR history.

7. Derrike Cope – 1990

Cope was a complete underdog who had never shown winning speed at the Cup level. He won when Dale Earnhardt cut a tire in the final corner after dominating the entire race.

6. Michael McDowell – 2021

McDowell had never won a Cup race in his career and often ran mid-pack. He missed the final-lap wreck and outran Team Penske to claim the victory.

5. Ward Burton – 2002

Burton was not considered a contender entering Speedweeks. Strategy, positioning, and late-race chaos helped him hold off stronger teams to take the win.

4. Jamie McMurray – 2010

McMurray had not won a race for three years and entered Daytona with modest expectations. He held off a late charge from Dale Earnhardt Jr. in a dramatic finish that shocked the field.

3. Sterling Marlin – 1994

Marlin drove for Morgan-McClure, a smaller team without the resources of the powerhouse organizations he beat. His win came through pure speed rather than luck, which made it even more surprising.

2. Trevor Bayne – 2011

Bayne was only 20 years old and racing in his second career Cup start. He held off multiple champions to give the Wood Brothers their most unexpected modern victory.

1. Derrike Cope – 1990

Cope’s win remains the most improbable result in Daytona 500 history. A driver with no wins and almost no national recognition beat the greatest driver of his era on the final turn.