10 Daytona 500 Losses That Absolutely Broke NASCAR Fans’ Hearts

Daytona 500 Losses That Absolutely Broke NASCAR

Dale Sr. and Dale Jr.

10. Dale Earnhardt – 1990

Earnhardt dominated the race, led late, and was cruising to a long-overdue win… until a flat tire with two laps to go. Derrick Cope slips by, and Dale’s Daytona curse lives on.

9. Mark Martin – 2007

This one still stings. Martin loses the Daytona 500 by 0.020 seconds to Kevin Harvick, the closest finish in race history. One more foot and Mark finally gets his crown jewel.

8. Tony Stewart – 2004

Stewart controls the race late, but a restart turns chaotic. Dale Earnhardt Jr. times the run perfectly, and Smoke is left watching yet another Daytona 500 slip away.

7. Jeff Gordon – 2007

Gordon led coming to the white flag, only to get swallowed by the draft in the final corner. A fourth Daytona 500 was there… and vanished in seconds.

6. Kyle Busch – 2019

Busch gets out-maneuvered on the final lap by Denny Hamlin. For a driver with championships and wins everywhere else, Daytona keeps saying “not today.”

5. Dale Earnhardt Jr. – 2011

Junior is in position to win, pushing the right line… when the big one erupts behind him. The caution freezes the field and hands the win to Trevor Bayne.

4. Rusty Wallace – 1998

Wallace finally looks ready to win his first Daytona 500—until Earnhardt charges through the field late. Rusty finishes second… again.

3. Carl Edwards – 2016

Edwards blocks aggressively on the final lap, gets turned, and crashes while leading. Denny Hamlin steals the win by inches in a photo finish.

2. Ryan Newman – 2020

Newman leads off Turn 4 on the final lap… and then gets launched into a terrifying crash. He survives, but the win slips away in one of the most chilling endings ever.

1. Dale Earnhardt – 1997

The most painful Daytona 500 loss ever. Earnhardt dominates, leads late, blocks perfectly—until a final-lap crash hands the win to Jeff Gordon. One year before Dale finally breaks through, this felt cruel.