From part-time drivers to underfunded teams, these five NASCAR underdogs didn’t just turn up: They walked in, shocked everyone and ripped up the script.
Every NASCAR season has its favorites. The big teams show up with all the money, the best crews and enough engineers to staff a rocket launch. And then there’s the rest; the longshots, the drivers people barely mention in pre-race picks. But sometimes, someone throws all that out the window.
For diehard fans, those “bracket buster” moments are magic. They’re the upsets that turn playoff brackets upside down, mess with everyone’s bets and remind us why we sit through every lap. In the era of NASCAR playoffs, a handful of drivers have pulled off wins that had no business happening. Here are five of the wildest bracket busters in recent memory, guys who ignored the odds and sent shockwaves through the sport.
1. Justin Haley – Daytona lightning strikes (2019)
No one expected Justin Haley to win the Coke Zero Sugar 400. Spire Motorsports? Come on. Haley was just getting his feet wet in Cup, learning the ropes. And then Daytona did what Daytona does.
Rain, wrecks, and chaos everywhere. While the favorites crashed out, Haley kept his nose clean. Suddenly, lightning forced NASCAR to call it. Haley, just 20 years old and not even a full-timer, was leading. He’d just beaten the biggest names in the sport.
Sure, you could call it lucky. But superspeedways reward survivors, and Haley put himself in position. Vegas didn’t see it coming. The garage didn’t either. This was a longshot win for the ages.
2. Chris Buescher – Bass Pro Shops Night Race (2022)
Short tracks are usually playgrounds for the heavy hitters; big teams, top drivers and all the resources. But at Bristol’s night race, Chris Buescher turned everyone’s expectations inside out.
RFK Racing wasn’t exactly in “powerhouse” mode back then. But Bristol that night? Pure chaos. Wrecks, tire blowouts and tempers everywhere. Buescher managed to stay out of trouble. He kept the car straight, played strategy just right and in the closing laps, he flat-out beat teams with way more money.
It reminded everyone, especially with the Next Gen car mixing things up, the gap’s not as wide as it used to be. One solid night can change everything. And for the folks who obsess over odds and strategy, this was the kind of win that scrambles everything. Betting sites such as Betting.net break down these upsets all the time, tracking how a single wild result can reshape the outlook. When Buescher took Bristol, you could feel the ripple.
3. AJ Allmendinger – The Roval redemption (2021)
Road courses are always unpredictable, but the Charlotte Roval? That place is mayhem by design. In 2021, AJ Allmendinger came back to Cup racing for a handful of starts with Kaulig Racing. No one had them down as a threat, not at this level.
But Allmendinger’s always been a road course specialist, and at the Roval, he showed why. Late-race restarts, playoff drama and drivers throwing elbows everywhere. Allmendinger just kept his cool. When he crossed the finish line first, it wasn’t just a feel-good story: It was a shot across the bow for every playoff hopeful.
He showed that having a specialty still matters. In a world where everyone’s supposed to be equal, being really good at one thing can still turn a race upside down.
4. Michael McDowell – Daytona 500 shock (2021)
Sometimes NASCAR just flips the script, and Michael McDowell’s win at the Daytona 500 was one of those moments. He’d been around for years, always grinding in average cars for Front Row Motorsports. People knew his name, sure. He was reliable and put in the work, but nobody really thought of him as a Daytona 500 winner. That just wasn’t his story.
But 2021 turned wild. Wreck after wreck thinned the field. On the last lap, the leaders tangled right in front of him. McDowell just kept his foot in it, dodged the chaos and suddenly he was crossing the line first. Biggest win of his life, no question.
The Daytona 500 always has a bit of chaos baked in, but come on, McDowell beating out the big teams like Hendrick and Joe Gibbs? That’s the kind of thing that changes a career in a single night.
5. Ross Chastain – Playoff mayhem at Martinsville (2022)
Now this one? Total madness. Ross Chastain showed up at Martinsville in the 2022 playoffs needing something wild to keep his championship hopes alive. He found it.
With just laps left in the Xfinity 500, Chastain floored it and rode the outside wall, literally, passing car after car in a move nobody had ever seen before. People started calling it the “Hail Melon” almost instantly. He didn’t win the race, but he completely blew up the playoff standings. Big names got bounced. Chastain kept his title shot alive.
From a betting angle, moments like that mess with every assumption about how a race is “supposed” to go. It was pure instinct, pure desperation, and it actually worked. Even the most jaded fans had to hit rewind just to believe what they’d seen.
Why bracket busters matter more than ever
NASCAR’s never been tighter. The Next Gen car shrank the gaps between teams. Everyone’s sharing data, running endless simulations. But the weird thing? Unpredictability isn’t going away. If anything, we’re getting more of it.
Underdogs break through. Strategies shake things up. Weather still throws a wrench into the works. Superspeedways are still the great equalizer.
For fans who care about the numbers as much as the drama, these upsets are gold. They make you question everything. They show just how thin the line is between a superstar and a guy having the night of his life.
