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The Daytona 500 has served as a triumphant occasion for many drivers throughout its colorful 64-year history. But for every triumph the 500 has yielded, there’s been at least one driver who’s left the 2.5-mile superspeedway feeling especially downtrodden about what could have been.

Up next, we’ll look back on the five most gut-wrenching defeats in nearly six-and-a-half decades of The Great American Race, ending with the one that stands as the greatest Daytona 500 sucker punch of all time.

5. Richard Petty’s loss to David Pearson at the 1976 Daytona 500

The only thing worse than losing the Daytona 500 on the final lap is losing it to your biggest rival. That happened for Richard Petty at the 1976 Daytona 500, a race he appeared poised to win over South Carolina’s David Pearson as the two approached the exit of Turn 4 on the final lap. After clearing Petty’s iconic blue No. 43 car coming down the backstretch, Pearson’s No. 21 Wood Brothers Racing car drifted high, allowing Petty to execute a bold crossover move to the inside. 

As Petty attempted to clear Pearson off Turn 4, the two cars hooked together and spun into the frontstretch grass just feet shy of the checkered flag. At first, it appeared that Petty would win the race since his car spun in the direction of the finish line and much closer to the checkered flag than Pearson, who slid down into the grass, but Petty ended up sliding into the grass himself before he could reach the finish line.

Despite his greatest efforts to get his car going again, Petty ended up stuck in the frontstretch grass — less than 100 yards from the flag stand — while Pearson managed to quickly refire his machine, pass the stalled car of Petty and take the checkered flag to earn what would be his first and only Daytona 500 victory. For Petty, who’d been in search of his sixth Daytona 500 win, this was a bitter pill to swallow and a result he’d always wish he could have back.

4. Cale Yarborough and Donnie Allison’s loss to Richard Petty at the 1979 Daytona 500

Often considered the most consequential race in NASCAR history, the 1979 Daytona 500 featured a bare-knuckle, last-lap battle for the lead between Donnie Allison and Cale Yarborough that culminated in the two drivers slamming together multiple times and spinning, which paved the way for Richard Petty to come from third to first and capture his sixth victory in The Great American Race.

After exiting their vehicles, Yarborough and Allison engaged in heated fisticuffs that captured the imagination of those in attendance and, more importantly, a live TV audience — the first live TV audience to ever watch a NASCAR race from start to finish. Donnie’s brother, Bobby — a future NASCAR Hall of Famer — also joined in on the fray in an effort to defend his younger sibling.

“And there’s a fight between Cale Yarborough and Donnie Allison,” legendary broadcaster Ken Squier proclaimed from the CBS broadcast booth. “The tempers overflowing. They’re angry. They know they have lost. And what a bitter defeat.”

3. Martin Truex Jr. and Matt Kenseth’s loss to Denny Hamlin at the 2016 Daytona 500

The final lap of the 2016 Daytona 500 had a Toyota flavor as the Toyotas of Matt Kenseth, Denny Hamlin, Martin Truex Jr., and Kyle Busch jockeyed for position at the front of the field.

For most of the white-flag lap, Kenseth appeared poised to snare his third Daytona 500 and first with Joe Gibbs Racing, but everything changed in turns 3 and 4 when the 2003 Cup Series champion went high to block teammate Hamlin.

This allowed Truex to jump to his inside, and Hamlin did the same when Kenseth’s No. 20 car wiggled and slid up toward the wall, leaving Truex and Hamlin to settle it in a drag race to the checkered flag that Hamlin won by one one-hundredth of a second — the closest margin of victory in Daytona 500 history. 

While Hamlin celebrated his first triumph in The Great American Race, both Truex and Kenseth were left to consider what might have been.

2. Mark Martin’s loss to Kevin Harvick at the 2007 Daytona 500

Five times a NASCAR Cup Series championship runner-up, Mark Martin endured far more disappointment and heartache in his career than the typical driver. But hands-down, the biggest heartache came at the 2007 Daytona 500, a race Martin led and seemed to be in control of when the field took the one-to-go flag.

With Martin appearing to be sailing toward a long-awaited first victory in NASCAR’s biggest race, the scenario shifted dramatically with less than half a lap remaining when Kevin Harvick gained a big head of steam down the backstretch and came roaring to Martin’s outside in the middle of turns 3 and 4. From there, it was a drag race to the finish line between the two drivers, with Harvick inching ahead at the last moment to edge Martin by two one-hundredths of a second.

Martin, who had led 26 consecutive laps prior to the final one, finished his career with 40 career Cup Series wins but none at Daytona — a place he’ll likely always remember most for the one that got away in 2007.

1. Dale Earnhardt’s loss to Derrike Cope at the 1990 Daytona 500

How does a driver not win the Daytona 500 after having a car so dominant that he leads at one point by as much as 40 seconds? That actually happened to Dale Earnhardt in 1990, and you can blame a piece of metal bell housing for his unfortunate demise.

After pacing the field for 155 of the race’s 200 laps, Earnhardt continued to hold the field at bay on the final lap when his iconic black No. 3 Chevrolet ran over the debris and slowed abruptly as it approached Turn 3 with a shredding right-rear tire. With Earnhardt fighting to keep the car off the wall, four drivers — led by unheralded Derrike Cope — moved to his inside and crossed the finish line ahead of him.

Earnhardt, who’d already endured a Daytona 500 heartbreaker in 1986 when he ran out of gas while leading with three laps to go, would go on to suffer several more painful outcomes in NASCAR’s “Super Bowl” before finally breaking through in 1998 in his 20th try.

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