The Daytona 500 is the most prestigious race in NASCAR, which means those who win it experience the highest high the sport can provide. But those who fall just short experience a heartbreak like no other. Here are the five most heartbreaking Daytona 500 losses in the race’s 67-year history. 

5. Dale Earnhardt, 1990 

Had Earnhardt not been able to finally conquer NASCAR’s greatest race in 1998, this entry would easily top the list. Earnhardt, who was already a three-time Cup Series champ and superspeedway ace by the start of the 90s, led the “Great American Race” going into the final corner of the 1990 edition and had led 155 laps on the day. But on Lap 200, he encountered a flat tire in Turn 3.Â