Bailey Wynkoop is a former NASCAR driver from Falls Church, VA. He competed in two Sprint Cup Series events in his career. Both races came in the 1958 season, when Wynkoop debuted at Manassas. Starting 13th in the field, Wynkoop completed all but twelve laps in route to a solid 12th place finish. Engine failure would prevent him from bettering that in his other race, finishing 22nd at Richmond.