Simon John Stapleton (born 10 December 1968) is an English former professional footballer who played as a midfielder. He spent the majority of his career at Wycombe Wanderers. Born in Oxford, Stapleton started his career as an apprentice at Portsmouth, before joining Bristol Rovers in 1988, where he made his Football League debut. He joined Conference side Wycombe Wanderers in 1989, where he helped the team win promotion to the Football League in 1992–93. During the same season, Wycombe also reached the final of the FA Trophy, but Stapleton did not play after failing a late fitness test.