The NASCAR Cup Series has seen 206 different drivers score at least one points-paying win during its 77-year history. But there are plenty of talented racers who never won.
Some of them just never got the right opportunity. Some of them never had the right luck. But all of them were ultimately left wondering what could have been.
With that in mind, let's count down the 10 greatest drivers in NASCAR history who never made it to Victory Lane at the top level. Active Cup Series competitors will not be included.
10. Ted Musgrave
Ted Musgrave was a champion in the Craftsman Truck Series in 2005, but before that, he was a Cup Series fixture during the 1990s. During five seasons with Roush Racing, he finished 16th or better in points four times, including a career-best standings position of seventh in 1995.
He compiled seven top five finishes that year, including runner-up results at Martinsville Speedway and Pocono Raceway. But he never won.
9. Matt DiBenedetto
Matt DiBenedetto was a fan-favorite in the late 2010s due to his outgoing personality and rags-to-riches story, slowly working his way from an underfunded field filler into a driver who could compete for wins. He landed himself a pair of quality rides with Leavine Family Racing and the Wood Brothers, and he qualified for the Cup Series playoffs in 2020.
His best chance at a win was in the 2019 Bass Pro Shops NRA Night Race at Bristol Motor Speedway, where he led a race-high 93 laps but was passed for the win late by Denny Hamlin. He has been back in the lower levels since 2022, after unceremonious exits with multiple organizations.
8. Dave Blaney
While his son Ryan went on to be a Cup Series champion, Dave Blaney had a career full of tough breaks. He consistently got the most out of his equipment during stints with Bill Davis Racing, Jasper Motorsports, and Tommy Baldwin Racing, earning a career-best finish of third on three separate occasions.
Blaney's biggest heartbreak came in the 2001 Cracker Barrel 500 at Atlanta Motor Speedway, when he led 70 laps and was running away from the field in the closing stages before a wheel fell off his car. He also might have won the famous finish in the 2003 spring race at Darlington Raceway had there been only a few more laps.
7. J.D. McDuffie
J.D. McDuffie was one of NASCAR's longest-running independent drivers during the 1970s and 1980s, and he holds the record for most career Cup Series starts without a win (653). In fact, he never even finished a race on the lead lap.
But he gets an A for effort. His small-time operation was enough to land him in the top 20 in points every year between 1969 and 1982, and he compiled 106 career top 10 finishes. His best race came at Nashville Speedway in 1979, when he accounted for 111 of his 162 career laps led and finished fifth.
6. Jeff Green
Jeff Green was a Busch Series (now O'Reilly Auto Parts) champion who never got the right shot in Cup until it was too late. He was 39 years old during his first full season in 2002, in which he impressively finished 17th in points for Richard Childress Racing during a down year for the organization. The next season, he was released after only 11 races following a dispute at Richmond with teammate Kevin Harvick.
He spent the rest of his career with middling organizations such as Petty Enterprises and Haas CNC Racing, with the occasional strong showing. He just needed an opportunity a few years earlier.
5. Banjo Matthews
Banjo Matthews is best known as the car builder for Junior Johnson's team during Cale Yarborough's run of three consecutive championships between 1976 and 1978. Prior to that, he was a part-time competitor on the Cup Series grid during the early 1960s, and he was exceptionally unlucky to never win.
His 495 career laps led ranks fourth among all winless drivers, and he accomplished it in only 51 career starts. Of those laps led, 163 came in the 1961 Dixie 400 at what is now EchoPark Speedway in Atlanta, but he blew an engine and finished 11th.
4. G.C. Spencer
G.C. Spencer was another independent driver of NASCAR's early years, and he holds the all-time record for most top five finishes (55) without a win. He was a staple of the Cup Series grid between 1959 and the late 1970s.
His most successful season came in 1965, when he recorded 14 top five finishes and finished fourth in points. He also earned 90 of his career 148 laps led that year. Still, a Cup Series win eluded him.
3. Dick Trickle
Ah, yes, the guy with the funny name who was known for smoking cigarettes behind the wheel. He was also a wildly successful regional short track racer, allegedly with more than 1,000 local wins to his resume. But in the Cup Series, he was one of the best drivers who never won.
Dick Trickle was one of the oldest rookies in Cup Series history, at the age of 47 in 1989. His best years were already behind him by that point, but he still had two semi-successful seasons with multiple top five finishes and at least 80 laps led. He continued to race at the top level throughout most of his fifties, even recording a pair of top five finishes as late as 1997 with Junie Donlavey's team.
Trickle might have won not just once, but many times, had he had a chance in Cup earlier in his life. Alas, it wasn't meant to be.
2. Joe Ruttman
Like Trickle and Green, Joe Ruttman bloomed just a few years too late. His first full season at the top level came in 1982, when he was 37 years old, and in 1983, he led 397 laps en route to a 12th place points finish. Of those laps, 350 came in the first 10 races of that year, after which he sat third in the standings, all while driving for Ron Benfield's mid-pack team.
Ruttman went on to have another solid campaign in 1986, with five top five finishes driving for Kenny Bernstein. But his time in Cup ran out before he could visit the winner's circle, though he did win 13 times during a successful Truck Series stint in the late 1990s.
1. Mike Skinner
Technically, the Cup Series' greatest winless wonder wasn't winless at all. Mike Skinner found Victory Lane five times at NASCAR's top level. The only problem is that those wins came in a Budweiser Shootout qualifier race, an All-Star qualifier race, a Daytona 500 Duel, and two exhibition events in Japan. None of them counted for points.
So instead, the 1995 Craftsman Truck Series champion has to settle for the unfortunate distinction as the best to never do it. He's the all-time leader in laps led by a winless Cup Series driver by a wide margin, with 1,029. He finished 10th in points in 1999 and 12th in 2000, and he accomplished this despite never having a full-time Cup ride until he was 40 years old.
Some guys just can't catch a break. Skinner was certainly good enough, but it never came together for him when there were championship points being awarded.
Honorable mentions: Ralph Earnhardt, Tommy Irwin, John Sears, Hut Stricklin, Rick Mast