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.
