“The biggest letdown I’ve ever had”: When Dale Earnhardt lost the Daytona 500 due to a tire cut in heartbreaking fashion

NASCAR legend Dale Earnhardt’s long and painful quest for an iconic Daytona 500 victory is one of the most famous sagas in NASCAR history. His 1990 Daytona 500 loss remains one of the most heartbreaking moments in sports history. Dale Sr. was on the verge of finally winning his first 500-mile iconic season-opener in 1990 until a flat tire issue ended his hope.

Leading with less than two laps to go, seven-time NASCAR Cup Series champion was contending for victory. Dale Sr. had dominated the race, leading 155 of the 200 laps, showcasing the speed of his strong #3 Richard Childress Racing Chevrolet. When he entered Turn 3 on the final lap, his #3 car’s right-rear tire suddenly deflated.

Derrike Cope, who was running second, took advantage of an Earnhardt’s misfortune and claimed the elusive victory. The #3 driver limped his damaged car across the finish line in fifth place, marking one of the most shocking upsets in NASCAR history.

After the race, Dale Earnhardt, who was known as “The Intimidator,” expressed his emotions on the devastating loss and described it as the biggest letdown he has ever had in his career.

Here’s what Dale Sr. said (via News & Record):

“We had a tire go right in front of the chicken-bone grandstands on the backstretch. I hit some debris, something. This is the biggest buildup and the biggest letdown I've ever had. They didn't outrun us; they just lucked into it. But that's racing.”

The victory marked Derrike Copes’ first career win in the NASCAR Cup Series.

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Has Dale Earnhardt ever won the Daytona 500?

Dale Earnhardt is regarded as one of the greatest NASCAR drivers of all time. In his 27-year-long NASCAR career, he registered 70 wins in the Cup series and seven Cup championships.

After coming close multiple times to Daytona 500 victory, Dale Sr. eventually conquered the Daytona 500 in 1998. It came in his 20th attempt after failing to win in the previous 19 attempts.

In addition to his maiden Daytona 500 win in 1998, he had scored five runner-up finishes and 12 top-five finishes.

Daytona 500, known as “The Great American Race,” is considered the most prestigious and important event, and it is held annually as the season-opener at Daytona International Speedway.

The 2025 Daytona 500 at Daytona International Speedway is set to be held this weekend, and fans can enjoy the action on FOX.