The 4 Flukiest Winners In Daytona 500 History and How They Managed to Shock The World

The Daytona 500 is by far the most prestigious race on the NASCAR Cup Series schedule. As a result, it’s also one of the hardest races to win.

Except when a driver comes out of nowhere to get a taste of Daytona 500 glory.

While plenty of the sport’s proverbial heavyweights have prevailed in the 500 over its illustrious 64-year history, this race — just like all the other ones on the Cup calendar — doesn’t always end with a big name in Victory Lane.

In fact, Daytona’s status as a 2.5-mile, high-banked superspeedway where drafting plays a key role in one’s success makes it even more likely than some tracks to produce a surprise winner.

With this in mind, up next is a hot take on the four all-time flukiest Daytona 500 champions (that’s what winners of the 500 are officially called) and how they managed to do the unthinkable against all odds.

Derrike Cope, 1990 Daytona 500 champion

To no one’s surprise, Dale Earnhardt arrived at the 1990 Daytona 500 with the car to beat — and once the green flag waved, the then-three-time Cup Series champion made sure to leave no doubt about it.

Starting second, Earnhardt needed only one lap to power his way to the front of the pack, where he spent the next 26 circuits in the lead. Driving his famed black No. 3 Chevrolet for Richard Childress Racing, Earnhardt went on to pace the field for a whopping 155 of 200 laps and build a lead of as much as 40 seconds. The Kannapolis, N.C. native appeared to have the race well in hand coming down the backstretch on the final lap before calamity struck in the form of a cut right-rear tire resulting from a piece of debris that he hit just before the entrance to Turn 3.

As Earnhardt fought to keep control of his car that drifted high toward the wall, four drivers moved past him on the inside — led by little-known driver Derrike Cope, who prior to 1990 had never run a full season or recorded a top-five finish in NASCAR’s premier series.

Cope went to Victory Lane a second time that year — in June at Dover — but never again triumphed at NASCAR’s highest level. In 428 Cup starts, he owns just the two aforementioned victories and four other top-five finishes. His best points finish — a 15th-place result — came in 1995. The California native has never formally retired from racing and still enters the occasional Cup event, but he does so as a start-and-park driver who pulls into the garage after just few laps and never returns to competition.

Ward Burton, 2002 Daytona 500 champion

Entering the 2002 Daytona 500, Ward Burton had just three NASCAR Cup Series wins over eight full or mostly full seasons at NASCAR’s highest level.

None of that mattered in The Great American Race, however, as Burton — a slow-talking native of the tiny town of South Boston, Va. — took the lead for the first time with five laps to go and held on from there. Sterling Marlin, who had the race’s dominant car, incurred a costly penalty from NASCAR for jumping out of his vehicle to clean off its front grille during a red flag period late in the race. 

Marlin recovered from the penalty to finish eighth, but it was Burton whole stole the day in his Bill Davis Racing ride and celebrated his first and only victory in the all-important season opener at The World Center of Racing.

Trevor Bayne, 2011 Daytona 500 champion

Using to his full advantage the then-current superspeedway rules package that created two-by-two “tandem” racing rather than the familiar big-pack racing seen over many years, Trevor Bayne scored an improbable Daytona 500 victory for the fabled Wood Brothers Racing organization in just his second career start in NASCAR’s top series.

Bayne was originally set to run just a third of the races that season in a part-time effort with the Wood Brothers’ iconic No. 21 Ford but ended up adding a handful of events after shocking everyone — including himself, it seemed — with his victory at the track built more than five decades earlier by the late NASCAR founder William H.G. “Big Bill” France.

“Are you kidding me?” Bayne exclaimed over his in-car radio after taking the checkered flag.

Bayne has yet to win another Cup Series race, however, and he never got promoted to a full-time ride in the No. 21 as so many expected he would after he delivered the Wood Brothers their 99th Cup Series victory but first since 2001.

Bayne, who led just the final six laps in the 2011 Daytona 500, eventually did go full-time Cup Series racing — but not until 2015 with Roush Fenway Racing.

Last season, Bayne concentrated his efforts in the NASCAR Xfinity Series, where he made nine cameo starts for Joe Gibbs Racing and earned seven top-10 finishes, five of them in the top five.

Michael McDowell, 2021 Daytona 500 champion

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The most recent Daytona 500 winner whose victory most would consider a fluke is 2021 Daytona 500 champion, Michael McDowell.

Heading into the race, the Cup Series veteran and Front Row Motorsports driver had exactly zero wins in 357 starts, making his chances of prevailing in The Great American Race virtually non-existent, at least from a statistical standpoint. What many didn’t realize, however, was that McDowell actually possessed a pretty decent record at NASCAR’s two superspeedways — Daytona and Talladega — well before he showed up to compete that day.

Nevertheless, no one expected him to prevail in the opening event of the 2021 season, and the manner in which he went about winning would, by all means, fall into the “fluke” category.

Just in case you’ve forgotten and weren’t watching: McDowell was third in line coming down the backstretch on the final lap when front-running teammates Joey Logano and Brad Keselowski got together and crashed, and the proverbial seas all but literally parted for McDowell’s No. 34 Chevrolet.

McDowell led just one lap on the day, but it was the most important one, and the veteran driver left Daytona with the coveted Harley J. Earl Daytona 500 winner’s trophy in his possession.