5 NASCAR veterans facing longest winless streak as Cup Series enters 2025 playoffs

The 2025 NASCAR Cup Series Playoffs begin this weekend with the Cook Out Southern 500 at Darlington Raceway, and the focus is on the 16 drivers competing for the title over the final 10 races. But outside the playoff spotlight, several familiar veterans are still chasing long-awaited victories.

Some have been close, others, rarely a factor, but each one of them is carrying a streak that has stretched deep into seasons past. These five names won't be factors in the title fight, but each carries motivation of a different kind.

Here are the five veterans with the longest active winless streaks in the NASCAR Cup Series as the postseason begins.

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Five NASCAR veterans with the longest winless streak in the Cup Series

#5 AJ Allmendinger - 46 races

AJ Allmendinger before the NASCAR Cup Series race at Nashville Superspeedway. Source: Getty

Kaulig Racing's AJ Allmendinger is back in the Cup Series full-time after balancing Xfinity and Cup duty in recent years, but results have not followed. His last Cup win came at the Charlotte Roval in October 2023, and nearly two full years later, he's still searching.

The No. 16 Chevrolet showed flashes early this year but has managed only a single top-five finish, a fourth-place at Charlotte, in 26 starts. With all three of his career Cup victories coming on road courses, his best chance remains the Roval in the fall, but with just one road course left, opportunities are limited.

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#4 Brad Keselowski - 49 races

Brad Keselowski (6) during the 2022 Pennzoil 400. Source: Getty

Brad Keselowski has had a frustrating 2025 campaign. The No. 6 Ford and co-owner of RFK Racing has been competitive in spurts with four top-fives, but mechanical issues and late-race fades have cost him shots at victory.

Keselowski sits outside the playoffs in 22nd place with 515 points, which reflects his inconsistency. The speed is occasionally there, but closing the deal remains elusive. The 2012 Cup champion last won at Darlington in May 2024 - a track he returns to this weekend.

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#3 Kyle Busch - 77 races

NASCAR Cup Series driver Kyle Busch sits in his Indianapolis garage. Source: Imagn

For the first time in his career, Kyle Busch endured a winless season in 2024, and now the streak has stretched into 2025. The two-time Cup champion last won at World Wide Technology Raceway in June 2023, and since then, the victories have dried up.

Busch's tenure at Richard Childress Racing has been rocky, and missing the playoffs in back-to-back years is uncharted territory for the driver with 63 career wins. He's still capable. Busch has won at nine of the 10 playoff venues on the schedule, but turning potential into results has been his undoing.

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#2 Michael McDowell - 80 races

NASCAR Cup Series driver Michael McDowell during Brickyard 400 qualifying. Source: Imagn

Michael McDowell made a name as a road-course specialist, but this year Spire Motorsports has often been overshadowed by Shane van Gisbergen's dominance on those layouts. McDowell has run up front, even leading in Chicago, Mexico, and Sonoma, but has just two top-fives to show for it.

His last Cup win came at the Indianapolis Road Course in August 2023, and as he turns 40, the chances won’t get any easier. For McDowell, the road courses were always his best shot, but without those opportunities, the path back to victory lane looks slim.

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#1 Erik Jones - 105 races

NASCAR Cup Series driver Erik Jones (43) before Go Bowling at The Glen. Source: Imagn

On top of the list is Erik Jones, who has not won since the Southern 500 at Darlington in September 2022. That victory was his third in the NASCAR Cup Series.

Driving for Legacy Motor Club, Jones has struggled to find speed and missed the playoff bubble entirely. A fifth-place finish at Daytona in the regular-season finale offered a glimmer of form, and returning to Darlington - the site of his last win - provides an opportunity to finally end a 105-race-long winless streak.