#5 Michael Waltrip.
Speaking of drivers that were only capable of winning on restrictor plate tracks and nowhere else, there’s also Michael Waltrip, who nabbed three wins throughout his entire Cup Series career and even went on to own a successful Cup Series team later on. Of course the team was forced to shut down after being dropped by several sponsors due to controversy, but he at least succeeded in a putting a competitive team together at times.
With that being said, and Michael Waltrip’s feats of brilliance at restrictor plates aside, he never found success at any other track on The Cup Series and retired from competition in 2007. He now serves as an analyst Fox Sports NASCAR broadcasts and does a segment called the grid walk before every Cup Series race on The Fox network.
In the end, Waltrip started his career in 1986 and couldn’t even nab his first of the four wins until The 2001 Dayton 500. Not only is that one of the worst winless streaks in all of NASCAR history it also comes from a guy that was the brother of future Hall of Famer, Darrell Waltrip, who finished his career with 50 wins and two championships.