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The Biggest Upset Winners of NASCAR’s Modern Era

The Biggest Upset Winners of NASCAR's Modern Era
Photo Credits to Sean Gardner and Chris Graythen/Getty Images for NASCAR

NASCAR

Where does Van Gisbergen Rank Among Surprise Winners Across NASCAR’s Modern Era?

To put it bluntly, last Sunday Shane Van Gisbergen scored an all-time great upset NASCAR win. A part-time team and a driver making his NASCAR debut stunned everyone on the streets of Chicago. How does Van Gisbergen’s win stack up against some other modern era Cup Series underdog victories? Here’s a few surprise drivers and teams who found victory lane in similar upsetting fashion.

Ron Bouchard – 1981 Talladega 500

One of a long list of surprise winners at Talladega is Ron Bouchard. The 1981 Rookie of the Year’s maiden season was capped off with a last-lap superspeedway stunner. While Hall of Famers Darrell Waltrip and Terry Labonte were blocking each other, Bouchard’s No. 47 Buick snuck by on the inside for a photo-finish win.

Waltrip later said he didn’t block Bouchard because he thought the 47 was a lap down. This would end up being Bouchard’s only career win across 160 starts.

Greg Sacks – 1985 Firecracker 400

A largely forgotten underdog modified driver, Florida native Greg Sacks has one career win on racing’s biggest stage. Ahead of the 1985 Firecracker 400 at Daytona, Sacks was asked to drive the R&D car for DiGard Racing. Sacks would be teammates with title contender Bobby Allison for this race.

In what was only supposed to be a start and park effort, Sacks kept the No. 10 Chevrolet in contention all day. Sacks eventually beat superspeedway ace Bill Elliott to the checkers, forever cementing his place in the record books.

Derrike Cope – 1990 Daytona 500

One of the biggest upsets ever in The Great American Race was Derrike Cope’s unlikely 1990 triumph. Dale Earnhardt dominated the 31st Daytona 500, leading 155 laps. On the last lap however, the No. 3 ran over some debris, causing a flat tire. In turn three The Intimidator slowed, allowing the Whitcomb Racing No. 10 Chevrolet to earn a spot in NASCAR history.

Cope would win later that season at Dover, but never again. Earnhardt’s famed Daytona 500 winless drought arguably came the closest to ending on this day in 1990, eight years before he finally found victory.

Trevor Bayne – 2011 Daytona 500

21 years after Derrike Cope’s mammoth-sized surprise win, another unknown took the path to Daytona 500 victory lane. Coming into the 2011 Daytona 500, very few eyes were on 20-year-old Trevor Bayne. Making only his second career start in the Wood Brothers No. 21, Bayne pulled off the unthinkable upset. NASCAR’s oldest team took their first victory in a decade.

Bayne was the beneficiary of an overtime blunder by David Ragan. The No. 6 Ford illegally changed lanes before the start/finish line, causing a penalty. The Tennessee native held off late charges from Carl Edwards, Bobby Labonte and Kurt Busch to become the youngest ever Daytona 500 Champion.

Further success has been fleeting in Bayne’s NASCAR career. Despite this, he has been attempting a racing comeback with any possible opportunity. Bayne did show potential in a few Xfinity starts last season with Joe Gibbs Racing.

Regan Smith – 2011 Southern 500

Only three months after Trevor Bayne’s triumph, another equally huge upset win happened with Regan Smith. Driving for then-underdog Furniture Row Racing, Smith took the No. 78 to its first win at Darlington Raceway. On old tires, Smith held off a hard charging Carl Edwards for the Denver, Colorado team’s first victory.

In the years since Smith has seen success in the Xfinity Series. Furniture Row also went on an unbelievable run with Kurt Busch and later Martin Truex Jr. The 78 team’s rise to stardom culminated with the 2017 Cup Series title. Alas, sponsorship woes forced the team to shut down in 2018. If not for Regan Smith’s upset win on The Track Too Tough to Tame, the huge success of Furniture Row Racing may have never happened.

2011 would see another trio of first-time upset winners. David Ragan got his Daytona redemption in that year’s Coke Zero 400 for his maiden win. Paul Menard also beat Jeff Gordon in a late duel at the Brickyard 400, and Marcos Ambrose took the checkers at Watkins Glen.

Justin Haley – 2019 Coke Zero Sugar 400

The most recent Independence Day weekend race at Daytona ended with a literal bang. After a vicious 18-car crash took out most of the pack, lightning put everything on hold. Left leading the few drivers remaining without damage was Justin Haley in the Spire Motorsports No. 77.

Still largely seen as an underdog team, Spire bought the assets left by Furniture Row Racing in 2018. In only his third career start, the 20-year-old was a Cup Series winner. By choosing not to pit and only leading one lap, the Indiana driver earned one of the biggest upset wins ever in NASCAR. Haley has been a full-time NASCAR Cup Series competitor since 2022, now with Kaulig Racing.

Shane Van Gisbergen – 2023 Grant Park 220

Heading into the first-ever NASCAR Cup Series street course race, nobody knew quite what to expect. Making his series debut in the Trackhouse Racing Project 91 Chevrolet, Shane Van Gisbergen was a highlight all weekend long. Fast in practice and qualifying, many were curious to see if the Supercars champion from New Zealand could pull off an unlikely upset.

Once the race began last Sunday the 91 was one of the best cars on the Chicago streets. Van Gisbergen was set back on an errant pit strategy, but began slowly moving forward. Four years after his above-mentioned upset win, Justin Haley was in position to steal another victory. The 91 however stalked down and passed the Kaulig Racing driver with eight laps left. Having to outlast an overtime restart, Van Gisbergen became the first Cup Series debut winner in 60 years.

SVG’s win is almost a historically-unmatched feat. A driver had not won a Cup Series race in start number one since Daytona Speedweeks in 1963. The street course specialist also earned the first road course ringer triumph in 50 years.

It is nearly impossible to classify all of these wins against each other; all of them had extenuating circumstances leading the upset team to the winner’s circle. Despite each race’s uniqueness, only Van Gisbergen had a perfect storm happen in his maiden start. We may not see another NASCAR feat this unprecedented for several years if not decades. In that aspect, Van Gisbergen had a moment rarely seen across sports with his accomplishment.

Written by Peter Stratta

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Photo Credits to Sean Gardner and Chris Graythen/Getty Images for NASCAR

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