NASCAR
Who Were the Biggest NASCAR Playoff Upsets From Win and You’re In?
Thanks to ‘The Chase’ returning as NASCAR’s championship format, the chapter is now closed on a truly unique era. For a dozen years, a single regular season win completely changed the trajectory of any team’s entire year. Any driver lucky enough to take a checkered flag in the opening 26 weeks was Playoff bound, with a shot at the championship. The revised version of the 2004-2013 points structure now renders ‘Win and You’re In’ a thing of the past. Over the last 12 years, here are the biggest surprise drivers who were able to win their way into NASCAR’s Playoffs.
2014
Amidst a radically redesigned points format in 2014, 13 drivers won their way into the new 16-man title dance. Two of these championship hopefuls were first-time Cup Series winners–Aric Almirola and AJ Allmendinger. Almirola and Richard Petty Motorsports took the July Daytona race, returning the iconic No. 43 to the grandest victory lane. Weather-shortened or not, nobody could rain on the parade of seeing Richard Petty back in Daytona’s winner’s circle 30 years after his 200th triumph. Almirola was 23rd in points when he was sent Playoff bound for the first time, and would finish 2014 ranked 16th.
‘The King’ Richard Petty standing with the Daytona winning trophies from the 1984 Firecracker 400 and the 2014 Coke Zero 400. Photo Credit: Brian A. Westerholt/Getty Images
A month later, AJ Allmendinger’s road course prowess reigned supreme at Watkins Glen. Marking the first career win for both Allmendinger and JTG Daugherty Racing, this race was an all-time classic. Allmendinger had to fend off fellow road course ace Marcos Ambrose, who was racing for an elusive Playoff berth in his final full-time NASCAR season. The No. 9 would not find a third Watkins Glen victory in four years, and had to settle for second that day. Meanwhile, Allmendinger took a maiden Playoff berth to a 13th-place points finish. Despite still racing Cup in 2026, 2014 remains AJ’s lone Playoff appearance to date. Allmendinger has though finished as high as third in the O’Reilly Auto Parts Series postseason.
2016
Ten years ago saw one of the weirdest and most circumstantial paths to the NASCAR Playoffs unfold. The August race at Pocono saw title heavyweights Joey Logano, Martin Truex Jr., and a still-winless Kyle Larson all dominate. Fellow contender Brad Keselowski was first to pit road under what appeared to be the final cycle of stops, though. The Penske No. 2 looked to be in position to steal this win, until his run was cut short. The caution flew for a massive fog bank blocking turns one and two, with Chris Buescher out front. At this time, Buescher was a Cup rookie in the Front Row Motorsports No. 34 Ford, and the reigning O’Reilly Series champion.
The fog never cleared up, forcing the Pennsylvania 400 to be called 22 laps short. This gave the ultimate underdog team a spot in 2016’s dance. Buescher locked in and redefined his 2016 season from 31st in the standings. The Cinderella run for team 34 would end with Buescher at 16th in points, but he has found far greater success in years since. The Texan has seen five more checkered flags to date with RFK Racing, piloting the No. 17 Ford since 2020.
I would be remiss to mention 2016 without also including Tony Stewart on this list. The three-time Cup champion and Hall of Famer did make the Playoffs in his last full-time season, after winning at Sonoma. Stewart famously knocked Denny Hamlin out of the way in turn 11 for his 49th and final Cup Series checkered flag. The flagship Stewart-Haas Racing No. 14 finished 2016 at 15th in points.
2017
The first year with Stage racing and tweaked Playoff bonus points, 2017 lives on in multiple aspects. Martin Truex Jr. and Furniture Row Racing both saw their dream championship season. This year was also the final laps for Dale Earnhardt Jr. and Matt Kenseth, sending off two of this era’s most popular drivers. 2017 likewise saw first career wins for Ricky Stenhouse Jr., Austin Dillon, and Ryan Blaney. Of those three new winners, only Dillon was outside of the top-16 in points (22nd) when he took the Coca-Cola 600.
22nd in points was the exact position for Kasey Kahne when he won the Brickyard 400. In what wound up being his final career win, Kahne outlasted Brad Keselowski in a marathon and carnage-filled double-overtime day. Kahne’s last year with Hendrick Motorsports saw him end 15th in points, while Dillon was 11th.
2020
The pandemic-defined season saw a rare occurrence unfold–a rookie winning their way into the Playoffs. Cole Custer was the ultimate upset victor at Kentucky Speedway, taking over with a bold last-lap four-wide pass. Custer was immediately vaulted from 20th in standings to the elite 16. Entering his rookie Cup campaign as a two-time Xfinity champion runner-up, this win changed Custer’s entire season. Four more top-10s sealed Rookie of the Year honors for Custer over a very stacked lineup of first-year drivers. Custer would go onto end 2020 at 16th in points.
Some would also label Austin Dillon’s 2020 Texas win as a Playoff-upsetting performance. Dillon’s third career win coincidentally happened the week after Custer’s Kentucky win. What few may remember, however, is that Dillon was in the Playoffs on points at this time. This win simply locked in the 3 team from 16th in the standings. Dillon would likewise wrap up 2020 ranked 11th once again.
2021
2021 had its fair share of surprise Playoff contenders early and often. The opening two weeks of this season saw two first-time winners: Michael McDowell at the Daytona 500 and Christopher Bell on the Daytona Road Course. Aside from these two, this season’s list of winners was fairly status quo, until New Hampshire in July. With darkness coming fast and Christopher Bell chasing him down, Aric Almirola scored perhaps the biggest upset win of 2021. This third career triumph for the Stewart-Haas Racing driver came amidst a horrendous season that saw him at 27th in points. Almirola and McDowell would respectively place 15th and 16th in 2021’s Playoffs. Bell, meanwhile, saw his maiden postseason run end in 12th-place.
2022
Year one of the Next Gen Car, 2022’s NASCAR season will live on for seeing an astounding 19 different winners. This increased competition tied the record for most Cup winners (2001) and saw only one man make the Playoffs on points (Ryan Blaney). 2022’s drivers who found victory lane included five first-time winners. This trend started off with rookie Austin Cindric winning the Daytona 500. Other newbies in that year’s Playoffs were: Ross Chastain, Chase Briscoe, and Daniel Suarez. Suarez’s maiden Cup triumph came that summer at Sonoma, when the Trackhouse No. 99 ranked 19th in points. This was the same spot where Austin Dillon was when he survived mayhem to win the Daytona summer race too. Sandwiched in between these two upset wins were Kevin Harvick’s last two career victories, coming back-to-back in August. Harvick won his way into Playoff status from 10th in overall points but 17th on the postseason grid. The highest finisher of these drivers was Chastain, who made the Championship 4 and was title runner-up.
2023
2023 can be characterized as another largely straightforward NASCAR Cup Series Playoff field. Ricky Stenhouse Jr. won the Daytona 500, but the No. 47 was already top 16 in points for most of the regular season. Aside from him, Michael McDowell at Indy in July was the only true upset winner. The road course ace took his second Cup triumph after a master performance, beating out Chase Elliott. McDowell and Stenhouse likewise were 15th and 16th in 2023’s final Playoff rankings.
2024
WorldWide Technology Raceway at Gateway was one driver’s Playoff Gateway after a bittersweet finish for Team Penske in 2024. Ryan Blaney was in command and en route to victory lane, but ran out of fuel on the last lap. This handed the win to teammate Austin Cindric, who took his second career Cup triumph in three years. Coming into this race, the No. 2 Mustang was 20th in points, and knocked out Chase Briscoe at the time.
The closing two weeks of 2024’s regular season saw two more successive upset winners. The Coke Zero Sugar 400 at Daytona saw perhaps the biggest underdog win in Playoff history, when Harrison Burton beat Kyle Busch to the checkers. This marked the 100th Cup win for the historic Wood Brothers Racing team, and was a first for young Burton. The second-generation star was 34th in points when he earned this breakthrough triumph, shattering many Playoff predictions.
The very next week saw Kyle Busch in the mix again but come home with another painful runner-up. The Southern 500 at Darlington saw Chase Briscoe beat the two-time champion for one final Stewart-Haas Racing win. Briscoe entered the Labor Day Weekend classic at 18th in points. The lame duck team was sent Playoff bound with an 11th hour victory in the regular season finale. The Cinderella run for Briscoe survived the opening round of eliminations, ending with a fitting 14th-place points finish.
2025
This past regular season saw domination by a few standout drivers. The opening 26 weeks earned four wins apiece for Denny Hamlin and Shane van Gisbergen. SVG’s road course mastery showed no signs of slowing down from Mexico City onwards. The 88’s first win saw him at 33rd in points, but the regular season ended with the Trackhouse driver ranked 24th.
Three more drivers did find victory lane from outside the top-16: Josh Berry, Austin Cindric, and Austin Dillon. Berry’s first Cup triumph came in week five at Las Vegas, taking the Wood Brothers back to victory lane for a second-straight year. Cindric meanwhile saw his superspeedway prowess reign supreme again at Talladega in April, taking a third win four years. Lastly, Dillon was victorious at Richmond Raceway for a second-straight season. No controversy this time, however, sent the 3 team to the Playoffs from this redemptive victory. SVG placing 12th in points was the best finisher for any of these drivers in 2025’s championship.
All of these aforementioned drivers saw their seasons defined thanks to ‘Win and You’re In.’ This mantra that was drilled into everyone’s heads over the past dozen seasons is no longer an upset’s path to Playoff glory. Instead, over half of Sunday’s grid will now be gunning for a coveted top-16 points berth after week 26. How these mindset and format changes alter drivers’ racing styles and what happens on-track all remain to be seen. Who the players are in the race for the final berths will be a fun story to follow along throughout this summer. In short, consistency has returned as the ultimate factor for making NASCAR’s Chase.
Written by Peter Stratta
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Photo Credits to Streeter Lecka, Rob Carr, and James Gilbert/Getty Images
