Petty took his number and sponsorship to Wood Brothers Racing in 1985, where he had a then career-high seven top-fives and his first top-ten points finish. The next season, he won his first career race in the infamous 1986 Miller High Life 400 at Richmond and finished tenth in the final standings. In 1987, he switched to the #21 and received new sponsorship from Citgo, as well as winning the 1987 Coca-Cola 600 at Charlotte. He failed to pick up a win in 1988, and fell to thirteenth in points, causing him to be released from the ride.