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Winning a NASCAR Cup Series race is often the pinnacle of a driver’s career. However, a few drivers have come painstakingly close to winning a race only to have it snatched away. These are the closest calls for the Cup Series’ best winless drivers.

• Drivers are only eligible for this list if they are winless in the NASCAR Cup Series. Even if they have won races in the lower series, they are still eligible for this list.
• This list will focus on the most heartbreaking losses. Whether they were the dominant car, yet failed to win, or if they came oh so close.
• Fans hate to see winless drivers come oh so close to a win. It’s as heartbreaking for fans as it is for the drivers in some cases.

Mike Skinner – 2000 Atlanta

Mike Skinner failed to win a Cup Series race despite his success in the lower series, but, he came incredibly close at Atlanta in 2000. Skinner led the most laps (191), and he seemed set on nabbing his first Cup Series win. That was until his engine blew up with 20 laps to go.

Skinner fell out of the race, and his teammate, Dale Earnhardt, took home the win in a photo finish over Bobby Labonte. A gutwrenching end for both Labonte and Skinner, but, especially Skinner, who failed to win a Cup Series race.

Matt DiBenedetto – 2019 Night Race at Bristol

Matt DiBenedetto’s 2019 loss at Bristol was disappointing at the time, but, it didn’t feel like the end of the world. It played a large role in getting the ride with The Wood Brothers for 2020, but, as it turns out, this was DiBenedetto’s best chance at a win. Looking back on it, it’s more heartbreaking than it was at the time.

DiBenedetto fought hard in the final laps with Denny Hamlin for the win. However, DiBenedetto couldn’t hold Hamlin off forever, and the win was Hamlin’s. DiBenedetto still remains winless in the Cup Series to this day.

Ted Musgrave – 1997 Michigan

Ted Musgrave later went on to be the NASCAR Craftsman Truck Series Champion, but, in the late 1990s, he was a young prospect driving for Jack Roush. His closest call came in 1997 at Michigan, when he led the most laps (68). However, pit strategy did him in.

Musgrave tried to keep the lead in the closing laps by stopping for fuel only, but, Ernie Irvan passed him. With no fresh tires, Musgrave fell back to 4th. He finished the race there.

Rick Mast – 1994 Rockingham

Rick Mast came close plenty of times, but none closer than in 1994 at Rockingham. The race came down to a battle between Mast and “The Intimidator”, Dale Earnhardt. In the end, it was Earnhardt who won by 0.06 seconds.

He only recorded 1 more top-5 finish in his career. Even if this was not a win, he went toe to toe with arguably the Greatest Of All Time, but, that doesn’t make it any less heartbreaking.

Kenny Wallace – 2001 Rockingham

Kenny Wallace rarely got an extended opportunity in top equipment, but, one came in late 2001. With Steve Park injured Wallace stepped in to race for the team at Rockingham. Park won at the track earlier that year.

Wallace started on the pole, and he led 101 laps. Unfortunately, he was outrun by another wild card driver, Joe Nemechek. Nemechek led 193 laps and took home the win over Wallace. It was the closest Wallace ever came to a win.

Close calls are a part of motorsports, and they always will be. These ones were perhaps the most heartbreaking.