Who doesn’t love a good underdog story? There is nothing better than watching the undersized or overmatched underachiever pull off an upset victory in miraculous fashion. It isn’t fun to sit and watch the same dominant drivers pull away from the field and win races by huge margins week in and week out. NASCAR is at its best when an unknown, or unsuspecting driver shows up in victory lane when it’s all said and done.
NASCAR has a great history of upset winners. There are surprise winners and total upsets every season across all of NASCAR’s national touring series. Whether it’s a young driver winning in just their second race, or a long-suffering veteran finally getting their first win, upset victories are part of what makes NASCAR great. Our rankings feature drivers who had help from mother nature, some dumb luck, a couple of savvy crew chiefs, and even some controversy. Here are NASCAR’s 20 great upset victories.
20. Derrike Cope – Daytona 1990
A lot of people are going to be mad that this isn’t higher, but this is where it belongs. If this were a list of absolutely ridiculous fluke victories, this would be number one, but we’re talking upsets here. Derrike Cope was essentially an unknown driver with just one career Cup Series top-ten finish before the 1990 Daytona 500. On the final lap, Cope would find himself in second place trailing the great Dale Earnhardt.
Unbelievably, Earnhardt would blow a tire and Cope would pass him and take the victory. Naturally, the win was a massive upset, as Cope was able to win NASCAR’s premier race in such spectacular fashion. I agree that this is a huge upset and belongs on this list, but not any higher than 20th. Winning due to someone else’s horrible misfortune is more of a complete fluke than an actual upset. But regardless what I think, Cope’s victory is often considered among NASCAR’s best upset victories.
19. James Buescher – Daytona 2012
Similar to Derrike Cope’s fluke victory, James Buescher’s 2012 Daytona victory also came under unbelievable circumstances. Buescher was racing part-time in the Xfinity Series for Turner Motorsports while also racing full-time for the Truck Series championship. At Daytona that year, Buescher would run mid-pack most of the day and found himself running in the 12th position on the final lap.
As the field headed into turn four, the four lead cars of Tony Stewart, Carl Edwards, Kurt Busch and Joey Logano all got into each other, leading to a massive pileup. Buescher, simply minding his own business, managed to drive through the smoke and debris and coast across the finish line for one of the weirdest upset victories in NASCAR history. Buescher wasn’t expected to do much in his part-time Xfinity Series gig, but he managed to win the biggest race of the season under incredible circumstances. Yeah, it’s a bit of a fluke, but he still had to avoid all those crashing cars to claim his upset victory.
18. Casey Mears – Charlotte 2007
The first few years of Casey Mears’ NASCAR career didn’t exactly go as he had hoped. After dismal overall points finishes his first three seasons, he’d have the best season of his career in 2006, finishing 14th in points. In 2007, things looked even better as he joined Hendrick Motorsports — NASCAR’s most successful team — to drive their No. 25 car. Heading into the Coca-Cola 600 at Charlotte, Mears had just one top-ten finish on the season and it looked as if it would be another disappointing year for him.
As the laps wound down, Mears’ crew chief told him to save fuel as they were going to forego a final pit stop and try and stretch their fuel to steal a win. The gamble paid off as Mears ran out of fuel just after crossing the finish line, securing his first and only career Cup Series victory. The win was a massive upset, as Mears was mostly an afterthought in the garage area; no one ever thought he’d have a real shot at a win. Although Mears’ wins was an upset, it isn’t higher on our list due to the sheer fact that he was driving for NASCAR’s best team. Had he pulled off this win in sub-par equipment, or with a smaller team, it would have been a much more impressive upset.
17. David Reutimann – Charlotte 2009
When David Reutimann was announced as one of the drivers for Michael Waltrip’s new Toyota powered Cup Series team in 2007, it left a lot of people scratching their heads. Reutimann had just one prior start in the Cup Series and hadn’t had much success as NASCAR’s lower levels. Naturally, 2007 was a dismal year and Reutimann failed to qualify for several races. He found a bit of footing in 2008 and by 2009, and was showing decent results.
At the 2009 Coca-Cola 600, Reutimann would do what most in the NASCAR community thought was impossible and win his first Cup Series race. The race was actually delayed by a full day due to rain and was held on a Monday morning. On lap 222, Reutimann’s crew chief Rodney Childers told him to conserve fuel in an attempt to take the lead when the other cars made pit stops. Childers had been watching the weather radar and saw that rain was coming. Five laps later, the rain came and delayed the race for several hours. Eventually NASCAR officials decided that it wasn’t possible to restart the race, handing the win to Reutimann who was scored as the leader.
NASCAR rules state that if half the laps in a race are completed and a rain delay occurs, the officials can decide to end the race if the rain shows no signs of stopping. This rule made one of the NASCAR’s most memorable upsets possible. David Reutimann would come out of nowhere to get his first Cup Series victory and spring boarded the win into several more successful years in the Cup Series.
16. Aric Almirola – Daytona 2014
Like David Reutimann’s victory at Charlotte, our 16th upset was also aided by mother nature. Aric Almirola has spent eight years racing in NASCAR’s top three series and by 2014 had cemented his status as an above-average driver in the Cup Series. Almirola is especially strong at Daytona and it was only a matter of time before he’d win a race there.
In the July 2014 race at Daytona, Almirola was up front for the majority of the night, battling in the top-five. He would eventually take the lead and on lap 112 rain began to fall causing NASCAR officials to stop the race. After a long rain delay, the officials deemed that they could not restart the race and Almirola was awarded the win. Now you have to consider that this win was aided by rain, but in all honesty even if it hadn’t rained, Almirola was in contention for the win and very well may have won the race anyway. Regardless, the win was considered huge upset and it was the first win for Richard Petty Motorsports at Daytona in 30 years.
15. Chris Buescher – Pocono 2016
In 2016, the reigning NASCAR Xfinity Series champion, Chris Buescher moved up to the Cup Series for his first season at NASCAR’s top level. Unfortunately, there weren’t a lot of seats that needed to be filled, so Buescher ended up driving for the small, low-budget two-car team of Front Row Motorsports. Buescher’s best finish in the first 20 races of the season was a 14th at Indianapolis. The next week at Pocono, Buescher would be having a usual race, running mid-pack and not at all in contention for the win.
As the field cycled through green flag pitstops late in the race, Buescher inherited the lead. At this moment, the heavens opened and rain soaked the racetrack. Since Buescher was the leader and the race was over halfway completed, he was ruled the winner. Yes, you have to consider the fact that the race was shortened by rain and it was a bit of a fluke that Buescher had the lead when it started raining. But rules are rules and Buescher got the win.
You could argue it was no more of an upset than the previous two rain-shortened scenarios, but you have to take into account that Buescher drove for a low budget team and was never expected to come close to winning a race. Even with the help of a few rain drops, Buescher’s victory at Pocono was quite the upset.
14. Robby Gordon – New Hampshire 2001
Controversy has followed Robby Gordon everywhere in his racing career and even his upset victory in 2001 is considered controversial. Before we get to the controversial part, let’s add some context to explain why this is such a great upset. Gordon tried and failed to become a full-time NASCAR driver on so many different occasions. He put himself back on the NASCAR radar after finishing second in a one-off race for Ultra Motorsports at Sonoma in June 2001. After an injury to Cup Series regular Mike Skinner, car owner Richard Childress tabbed Gordon to act as his replacement for several races.
Gordon came close to winning at the Watkins Glen road course a few races later but was taken out of contention due to a fire in his car started by the onboard camera. At the final race of the season at New Hampshire, Gordon would find himself racing the other Gordon (Jeff) in the waning laps. With 16 laps to go, Robby pulled up to Jeff’s bumper and knocked him out of the way to take the lead. Robby would hold on for the upset win, the first of his career.
Many drivers and media members felt that Robby’s move to bump Jeff out of the way was needless and probably a little dirty. Regardless what everyone else thought, Robby pulled off one of NASCAR’s greatest upsets and the win earned him a full time ride with Richard Childress Racing and a long career in NASCAR.
13. Brandon Whitt – Memphis 2005
If you’re a casual NASCAR fan, you’ve likely never heard of Brandon Whitt. Whitt drove full-time in NASCAR’s Truck Series in 2004 and 2005. He had very little success, registering just five top-ten finishes in 58 career races. At Memphis Motorsports Park in 2005, Whitt would shock the NASCAR community by winning the pole position for the race. Whitt maintained great track position throughout the race and was in contention for the victory with just a few laps to go.
What made matters even more remarkable was that the cooling systems in Whitt’s truck were malfunctioning and he was essentially being cooked by the heat in his truck as he drove around the track. On the final lap, leader Ron Hornaday spun out and Whitt was able get by him cleanly and take the win. Whitt collapsed in victory lane from heat exhaustion and had to be taken to a local hospital for treatment. This victory would be the only highlight of Whitt’s career and he would be completely out of NASCAR by the end of the 2009 season. Regardless of his overall career, Whitt’s victory is still thought of as one of the Truck Series’ biggest upsets.
12. Regan Smith – Darlington 2011
Regan Smith’s NASCAR career has had some massive peaks and some massive valleys. But Darlington 2011 was from the latter category. In 2011, Smith drove for a small single-car team, Furniture Row Racing. Yup, you guessed it, the team is owned and sponsored by a furniture company. Smith was into his second full season with the team and they’d had just one top-ten finish.
At Darlington, Smith seemed destined for the best finish of his career and had a very strong car. During a late-race caution, Smith’s crew chief made the call to stay on the track and not pit for fresh tires. The gamble paid off as Smith was able to hold off the hard-charging car of Carl Edwards for his first Cup Series victory. The win was monumental for both Smith and the Furniture Row team. Neither was ever expected to be a success in NASCAR and the win proved the doubters wrong. Smith has since enjoyed a long career in the sport and Furniture Row Racing won its first championship in 2017.
11. Brad Keselowski – Talladega 2009
Brad Keselowski had made just three career Cup Series starts when he headed to Talladega in 2009. He was a full-time driver in NASCAR’s lower-tier Xfinity Series and was racing part-time in the Cup Series for Phoenix Racing. Keselowski rode around about mid-pack for the majority of the race, hoping to avoid crashes and be around at the end of race for a shot at the win.
With two laps to go, Keselowski pushed Carl Edwards to the front and the two ran nose-to-tail until the final straightaway. Keseloski faked a move to the outside of Edwards, causing him to block, leaving the bottom of the track clear for Keselowski to make the pass. When Edwards attempted another block, the two drivers made contact sending Edwards airborne and careening into the oncoming car of Ryan Newman. Keselowski would manage keep his car going straight and take the win. It was a massive upset for the single-car Phoenix Racing team and the first win for team owner James Finch after 20 years in the sport. Keselowski would go on to win the 2012 Cup Series championship and is now a perennial title contender. But his first win in the series is an unforgettable one.
10. Michael Waltrip – Daytona 2001
Before the 2001 season started, Michael Waltrip had raced in 462 consecutive NASCAR Cup Series races without recording a victory. That would all change at the 2001 Daytona 500. Waltrip was hired by Dale Earnhardt to drive his new No. 15 car in 2001 as a teammate to his son, Dale Earnhardt Jr.
Waltrip was coming off a mostly down season the year prior and honestly, not much was expected of him. He would find himself leading the race in the final laps, being pushed around the track by his teammate Earnhardt Jr. On the final lap, Waltrip and Earnhardt Jr. would hold off the rest of the field and Waltrip would take the checkered flag for his first Cup Series victory.
The win was a massive upset for a driver that most thought would never win a race. But Waltrip’s upset victory was quickly overshadowed by the last-lap crash that killed his team owner Dale Earnhardt. Although the 2001 Daytona 500 is remembered as a day of tragedy, it is also the day that Michael Waltrip pulled off one of NASCAR’s greatest upsets.
9. Justin Labonte – Chicago 2004
As the son of two-time NASCAR Cup Series champion Terry Labonte, Justin Labonte had big shoes to fill. Justin began racing in NASCAR’s Xfinity Series in 1999 and made several starts each season for the next five years, all without success. In 2004, Justin was slated for another limited schedule and after seven races, his best finish was 18th. In his eighth race at Chicago, Labonte would do what absolutely no one thought was possible.
In the final laps of the race, several drivers tried to stretch their fuel to take a shot at the victory. On the last lap, race leader Mike Wallace would run out of fuel, handing the lead to Labonte. Labonte was able to save enough fuel to coast across the finish line and take the win. Sure, a lot of the credit should go to Labonte’s crew chief for engineering the strategy that won the race, but Labonte was the one behind the wheel.
The win was the highlight of Justin Labonte’s career, and he would be out of NASCAR by 2007. Although his career was mostly disappointing, Labonte will always be remembered for his upset at Chicagoland Speedway.
8. Wendell Scott – Jacksonville 1964
Wendell Scott was NASCAR’s first trailblazer. He was the first black driver to compete at NASCAR’s highest level and was the first (and still the only) to win a Cup Series race. Scott started racing in NASCAR in 1961, and spent 12 seasons in the sport. But Scott didn’t have to just fight for positions on the track, he also had to fight for respect and acceptance from other drivers and the sanctioning body.
Scott was refused entry to several races simply for being black and was told on many occasions that “black drivers aren’t allowed.” Despite this racism, Scott fought on and competed in 495 career races. In 1964, at the third race of the season, Scott would pass Richard Petty with 25 laps to go and cross the finish line first. But Scott wasn’t ruled the winner. The history is unclear on the reason why Scott wasn’t awarded the win, but many believe it was due to the racism of the times. Second place finisher Buck Baker was ruled the winner, but TWO YEARS later NASCAR would award Scott the victory. To make matters worse, Scott’s family didn’t receive the trophy until 2010, 20 years after Scott had passed away.
Wendell Scott’s victory at Jacksonville is one of NASCAR’s great upsets not only due to Scott’s low budget operation and sub-par racing equipment, but also due to how Scott was able to overcome racism and bigotry and fight for his place among NASCAR’s elite.
7. Jamie McMurray – Charlotte 2002
During the 2002 season, Jamie McMurray was tabbed by Chip Ganassi to drive a new car, the No. 42, in the Cup Series in 2003. In preparation, he was to make a few starts at the end of the 2002 season. But Ganassi’s other Cup Series driver Sterling Marlin was injured in a crash and McMurray was tabbed as his replacement. He would make his first start at Talladega and finished 26th. The next week at Charlotte, McMurray would pull off one of the greatest upsets in NASCAR history.
McMurray would battle with Tony Stewart and Bobby Labonte for the second half of the race and be squarely in contention for a top-five finish. McMurray would end up leading 96 of the last 100 laps and win the race, completing the upset. It was mind boggling for both fans and media alike to see McMurray take the checkered flag. It was the first time in NASCAR history that a driver won in their first race at a 1.5-mile speedway. After the upset, McMurray would make six more starts in 2002 and has been a mainstay in NASCAR since.
6. Kevin Harvick – Atlanta 2001
After the tragic passing of Dale Earnhardt in the 2001 Daytona 500, Kevin Harvick was tabbed by team owner Richard Childress to take over Earnhardt’s car. The car was renumbered 29 and given a white paint scheme to honor Earnhardt (who usually drove a black car). Harvick was a full-time driver in NASCAR’s lower-level Xfinity Series at the time and wasn’t expected to do much in the Cup Series due to being moved up so quickly.
At Atlanta in 2001, just Harvick’s third start, he would find himself in contention for the win in the final laps. It came down to a shootout between he and Jeff Gordon for the win. On the final lap, Gordon would take the high side of the racetrack to try and pass Harvick, but Harvick would manage to win the drag race to the finish and take the victory.
It was an incredible upset, considering Harvick had only two prior Cup Series starts and that he managed to beat former series champ Jeff Gordon. The win wasn’t only a great upset, it was also the perfect way to honor the memory of the great Dale Earnhardt, just three weeks after his passing.
5. Jeremy Clements – Road America 2017
Jeremy Clements has spent the last ten years racing in NASCAR’s Xfinity Series for his family owned team. In his 266 career races, Clements has just 13 top ten finishes, a few of which have come at the series’ road course races. In 2017, Clements would head to the final road course race of the season at Road America looking to simply have a clean race and maybe get a top ten finish. You see, Clements’ team has only a few race cars in their shop and even builds their own engines. They have a fraction of the budgets of the big teams, but it didn’t matter on this particular day.
Road course races are usually pretty crazy, especially at Road America. The track is nearly five miles in length and drivers are constantly getting in accidents and going off track, making for some unusual finishes. With two laps to go, Clements was running second behind Matt Tifft. Clements closed the gap as they approached the final turn of the second-last lap. Clements over drove the corner and made contact with Tifft, causing them both to spin out.
Luckily, the third place car was very far behind and Clements was able to get going again and complete the last lap for the win. It was the first win for an independent NASCAR team since David Gilliland’s win in 2006. Clements was emotional in victory lane and reminded the fans how much his team could get done with what little they have. The win was one of the most feel-good upsets in NASCAR history.
4. David Ragan – Talladega 2013
Some would argue that this one should be higher, but I’d have to disagree due to one variable. The draft. At Talladega and Daytona, NASCAR mandates that a restrictor plate gets put on every car. These plates limit air intake to the engine and slows the cars down. To combat this slowdown, drivers use aerodynamics to gain speed. Cars will drive around the track following each other in large packs, drafting off of one another to go faster. The draft levels the playing field for everyone. Even drivers in much slower, underfunded cars can draft with the powerhouse teams and get an upset victory.
That is exactly what happened to David Ragan in 2013. Ragan drove for the small, underfunded Front Row Motorsports team. Ragan was pushed across the finish line by his teammate David Gilliland to claim the victory and one of NASCAR’s greatest upsets. I’m not taking anything away from the feat, I love a good underdog story. But let’s face the facts: drafting made this possible. In his career with Front Row Motorsports, Ragan has eight top-ten finishes, seven of which have been at Daytona or Talladega. Without the draft, this upset would have never happened. It’s still a great story, but it comes in at number four.
3. John King – Daytona 2012
Ever heard of John King? No? Don’t feel bad. Almost no one had heard of John King before the Truck Series’ Nextera Engergy Resources 250 at Daytona in 2012. King had just seven NASCAR starts under his belt, all in the Truck Series. King drove for powerhouse team Red Horse Racing and had a fast truck throughout the entire race. He was actually caught up in two different incidents and sustained some damage to his truck, but he was able to keep going.
The race would end under overtime conditions due to several caution flags in the final laps. On the third overtime restart, King would find himself in the lead, being pushed by teammate Timothy Peters. After King took the white flag for the final lap, another on-track incident brought out the caution flag. Since King had taken the white flag, the race ended under caution and he was ruled the winner. The win transformed John King from complete unknown to a superstar. But unfortunately for King, his team would suspend operations after just four more races due to a lack of sponsorship and King hasn’t raced in NASCAR since 2014. Even though King’s career lasted just 15 races, his 2012 victory at Daytona is one of the best upsets in NASCAR history.
2. Trevor Bayne – Daytona 2011
Before the 2011 Daytona 500, Trevor Bayne had driven in just one NASCAR Cup Series race (the previous year at Texas). Bayne became a talking point at Daytona Speedweeks in 2011 after pacing the field during practice sessions and looking good in his qualifying race. Even four-time champion Jeff Gordon stated that Bayne may have the car to beat.
Well, Bayne did in fact have the car to beat.
Bayne would be the leader after the final restart with two laps to go. Off of the final turn, it was a four horse race between Bobby Labonte, David Gilliland, Carl Edwards, and Bayne. As they approached the finish line, Edwards pulled out to pass and Bayne executed a perfect block and held on for the win. Bayne’s win made him the youngest winner in Cup Series history at 20 years and one day. To this day, it is still Bayne’s only victory in the series but is one of NASCAR’s greatest upsets.
1. David Gilliland – Kentucky 2006
Like a lot of the other upset drivers on this list, no one had ever heard of David Gilliland before the Xfinity Series race at Kentucky in 2006. At the time, Gilliland had driven just seven NASCAR races in his career, six in the Xfinity Series and one in the Truck Series (with a best finish of 22nd). In 2006, Gilliland was racing for an unknown team of Clay Andrews Racing. The team had just a couple of racecars and even built their own engines.
At Kentucky, Gilliland would qualify in the fourth position, garnering attention from the NASCAR community. It was a great effort, but many saw it as a fluke. As the race unfolded, Gilliland was in the top ten most of the night and as the laps winded down, he was in contention for the win.
With eleven laps to go, Gilliland took the lead from J..J Yeley and he would not relinquish it. Gilliland would win the race, absolutely shocking the NASCAR community. Gilliland became the best thing since sliced bread and was racing for Robert Yates Racing in the Cup Series just a few weeks later. It was the start of a long career in NASCAR for Gilliland and is widely known as the greatest upset in NASCAR history.