4 Biggest Upsets in Daytona 500 History

Updated: November 30, 2023

The Biggest Upsets in Daytona 500 History.

The history of the Great American race is one filled with heartbreaks, triumphs, come from behind wins and spoilers that no one ever saw coming. This unpredictable quality is one the things that make the Daytona 500 the greatest event in stock car racing.

When the green flag drops on the Super Bowl of Stock Car Racing, you know that there are 40 drivers who really do have a shot at glory that day which, if we are to be entirely honest, is not something you can say about most races.

4 Biggest Upsets in Daytona 500 History

The Daytona 500 has seen many upset winners. Here are a few of the most memorable.

Trevor Bayne takes the Harvey J. Earl trophy on his 20^th birthday

Likely there was no one in the grandstands, or watching at home for that matter, who wasn’t at least a little happy to see rookie Trevor Bayne score a sensational victory in the 500 by beating out veterans Carl Edwards, Bobby Labonte and Kurt Busch.

Needless to say no one would have picked Bayne to win, as no rookie had ever won the race at point – nor has one done so since. Bayne is also the youngest driver to win the race.

Michael McDowell makes good…finally

Up until winning the 2021 500, the longtime Cup Series veteran’s only claim to fame had been a spectacular qualifying crash in 2008 at the Texas Motor Speedway which saw McDowell’s car barrel-roll numerous times.

His Daytona 500 victory was equally spectacular as Mcdowell drove past a fiery turn 3 melee to take a checkered flag that had been fourteen seasons in the making.

If history repeats itself, it may prove to be an even bigger upset than McDowell's first 500 win.

Derrick Cope steals one

Cope was a long shot to win the 1990 race, to say the least. But when Dale Earnhardt cut a tire in turn 3 of final lap, Cope inherited the lead with no competition anywhere in sight and cruised to his first win…and into the annals of Daytona 500 history.

Some might say he was just lucky, but the fact is he had earned the position he found himself in that day when the no.3 abruptly fell off the pace.

At any rate, Cope’s win was inarguably one of the biggest upsets in in the history of the race.

Michael Waltrip silences the doubters

The 2001 Daytona 500 will always be remembered as one of the sport’s darkest days, and the first of Michael Waltrip’s two victories in the Great American Race will always be overshadowed by the tragedy that unfolded on the last lap of that event.

Which is a shame for the younger Waltrip, who had been the losingest driver in the sport up till that point – a fact which many in the Nascar community didn’t let him forget.

While “Mikey’s” second Daytona 500 victory may have been sweeter for the Owensboro driver, his first will always be one of the biggest Daytona 500 upsets.

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