Winning a NASCAR Cup Series race isn’t easy, and for some drivers, it took hundreds of starts to finally claim victory. From last-lap drama to dominating performances, each of these wins was unforgettable. Whether at Daytona, Martinsville, or Charlotte, these drivers proved that perseverance pays off in the most spectacular way.

200-300-400 Races? Here are 10 Drivers Who Had to Wait the Longest for Their First Win

On Oct. 15, 2001, Ricky Craven finally broke through at Martinsville Speedway, taking his No. 32 Tide Ford to Victory Lane. Leading 94 laps, he held off Dale Jarrett in the closing stages. Before this win, his best Cup finish was second, which he had secured just seven weeks earlier at Michigan. Craven would win only one more Cup race in his career.

10. Ricky Craven (174 Starts)

On Sept. 19, 1999, Joe Nemechek finally tasted victory at New Hampshire. He held off Tony Stewart and Bobby Labonte following a late restart, leading 72 laps to secure his first Cup Series win. It was a long-awaited moment for Nemechek, who would go on to earn four career Cup victories.

9. Joe Nemechek (180 Starts)

James Hylton claimed his first Cup Series win at Richmond Raceway in 1970, leading 160 of 500 laps. He managed to beat Richard Petty, who was the only other driver on the lead lap. This was the first of only two career wins for Hylton, but it solidified his place in NASCAR history.

8. James Hylton (187 Starts)

On Aug. 10, 2014, A.J. Allmendinger outdueled Jeff Gordon to win at Watkins Glen. Leading 29 laps, he held off one of NASCAR’s best road racers to secure not only his first win but also the first victory for JTG Daugherty Racing. His breakthrough moment made him a favorite on road courses for years to come.

7. A.J. Allmendinger – (213 Starts)

Future NASCAR Hall of Famer Buddy Baker finally found Victory Lane on Oct. 15, 1967, at Charlotte Motor Speedway. Driving the No. 3 for Ray Fox, Baker led a race-high 160 laps and finished as the only driver on the lead lap. This was just the beginning of his legendary career.

6. Buddy Baker (216 Starts)

Johnny Benson Jr. won his first Cup race on Nov. 3, 2002, at Rockingham. Low on fuel, he managed to hold off Mark Martin in the closing laps. Taking the lead with 28 laps to go, he never looked back, earning his first and only Cup victory in the No. 10 Pontiac.

5. Johnny Benson Jr. (226 Starts)

On Sept. 28, 1975, Dave Marcis finally captured his first Cup win at Martinsville Speedway. Holding off Benny Parsons, he led 52 laps to claim victory in the Old Dominion 500. This was the first of five career wins for Marcis, who became known for his toughness and longevity in the sport.

4. Dave Marcis (227 Starts)

After years of coming close, Sterling Marlin finally earned his first career win in the 1994 Daytona 500. Driving for Morgan-McClure Motorsports, Marlin started fourth and led 30 laps, holding off Ernie Irvan in the closing stretch. He went on to win 10 Cup races, including another Daytona 500 in 1995.

3. Sterling Marlin (279 Starts)

Michael McDowell waited nearly 14 years for his first Cup victory, finally winning the 2021 Daytona 500. Running third on the final lap, he took the lead when Joey Logano and Brad Keselowski wrecked in front of him. When the caution flag waved, McDowell was out front, capturing an emotional first win in NASCAR’s biggest race.

2. Michael McDowell (358 Starts)

Michael Waltrip’s first win was both historic and heartbreaking. After 463 starts, he finally won the 2001 Daytona 500, driving for Dale Earnhardt Inc. With teammate Dale Earnhardt Jr. pushing him, Waltrip took the checkered flag. However, the celebration was muted due to the tragic loss of Dale Earnhardt in a last-lap crash. Waltrip went on to win four Cup races, all on superspeedways.