Thousands of drivers have made starts in the NASCAR Cup Series over the years, but five have cemented themselves as the winningest in the sport’s history. These are the five winningest drivers in NASCAR Cup Series history and the stories behind their legendary careers.
1. Richard Petty (200 wins)
There’s no denying that Petty earned his nickname of “The King.” Not only did Petty win 200 races at the Cup Series level, but he also won seven Daytona 500s and seven Cup Series championships. In 1967 alone, Petty won 27 of the 49 races on the schedule en route to his second championship – including 10 races in a row, a mark that still stands today. Petty sits 95 wins ahead of second place on the all-time wins list, and his all-time mark of 200 victories is unlikely to ever be challenged.
2. David Pearson (105 wins)
Known as “The Silver Fox”, Pearson was famous for saving his best for last. His relatively conservative driving style helped win win 105 races and three Cup Series championships. His biggest rival? The aforementioned Petty, who dueled Pearson to a 1-2 finish 63 times. Pearson holds a 33-30 edge in those 1-2 finishes, including a thriller in the 1976 Daytona 500 that saw Pearson limp across the line to earn his only victory in the ‘Great American Race.’
3. Jeff Gordon (93 wins)
How good was Jeff Gordon in his prime? It took him less than eight full-time seasons for him to win his 50th Cup Series race at Talladega in April of 2000. Gordon also won four Cup Series championships in just seven seasons (1995, 1997, 1998, 2001) and won three Daytona 500s (1997, 1999, 2005) in a legendary career. However, it was Gordon’s final victory that was perhaps the most memorable of his career. At Martinsville in November of 2015, Gordon won at Martinsville in his final full-time season to clinch a spot in the Championship 4. While he didn’t win his fifth title, the victory meant one of NASCAR’s greatest went out with a bang.
4. Bobby Allison (85 wins)
It wasn’t until October of 2024 that Allison officially earned his 85th win, but the 1983 Winston Cup Series champion would’ve made the list regardless. Allison was one of the few drivers to consistently challenge the likes of Petty and Pearson, and thrice saw victory lane at the Daytona 500 (1978, 1982, 1988). Allison passed away on November 9, 2024, but his Hall of Fame legacy will forever be remembered.
5. Darrell Waltrip (84 wins)
Ironically, the victory Allison was awarded 53 years after the race in question moved him ahead of one of his biggest rivals in Darrell Waltrip on the all-time wins list. That doesn’t negate Waltrip’s legacy, however, as ‘Jaws’ still put together one of the greatest careers in NASCAR history. Waltrip’s vibrant personality graced victory lane 84 times, including a win at the 1989 Daytona 500. Waltrip also won three Winston Cup Series championships with Junior Johnson, cementing his partnership with Johnson as one of the greatest driver-car owner duos in NASCAR history. After retiring from driving at the end of the 2000 season, Waltrip became a legend to a new generation of fans as an analyst for FOX’s NASCAR coverage, a job he kept until retiring in 2019.
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