at Pocono, Shepherd took his second pole of the year. After posting two top-tens in the No. 88 Oldsmobile for Buddy Baker, Shepherd finished out the year in his own No. 57, before his team was purchased by RahMoc for the season finale. He returned to RahMoc for the 1989 season. Shepherd scored thirteen top-ten finishes during the season. He led the most laps at the Talladega DieHard 500 but eventually finished the race in sixth place. Shepherd took his final career pole at Watkins Glen. He led the early parts of that race but lost his chance of winning the race after contact with Geoff Bodine. Shepherd's best finish of the season was two second-place finishes at the Pepsi 400 and the Champion Spark Plug 400. It was only the second time in his career Shepherd competed in every scheduled event. He finished thirteenth in the final points standings. Shepherd moved to Bud Moore Engineering for the 1990 season, driving the No. 15 Ford. He had a great start to the season finishing in the top ten in each of the first eleven races. Shepherd took the championship lead for the first (and only) time in his career after the Budweiser 500. He had a difficult midseason, losing the points lead and dropping to tenth in the standings after the Tyson Holly Farms 400. Shepherd ended his season on a high after winning his third career race at the season finale at Atlanta. He finished fifth in the final points standings, which would turn out to be a career-high. He stayed with Bud Moore for the 1991 season, but had a more up and down season than the year before. Although Shepherd scored fourteen top-ten finishes he could not compete for regular top-five finishes during the season. His best finish of the season was two third-place finishes late in the season. He had his best run of the season at North Wilkesboro, where Shepherd led a total of 41 laps and just missed out on the win. Shepherd dropped to twelfth in the final points standings. After the season Shepherd left Bud Moore Engineering and moved to the Wood Brothers for the 1992 season. Wood Brothers Racing Shepherd joined Wood Brothers Racing in 1992, driving the No. 21 Citgo Ford. He came short of winning the Daytona 500, finishing second to Davey Allison. Even though Shepherd scored eleven top-ten