Throughout his career Stapleton played for the Chicago Blackhawks, Pittsburgh Penguins, Edmonton Oilers, Winnipeg Jets, Phoenix Coyotes, Atlanta Thrashers, New York Islanders and Vancouver Canucks.

The son of former NHL player Pat Stapleton, he also played internationally for Canada at the 1986 World Junior Championships, winning a silver medal.

He was rated OHL Leyden Division's hardest worker, best faceoff man and best penalty killer in a 1985–86 poll of league coaches.

Stapleton served as an assistant to head coach/GM Scott Gardiner with the NAHL's Traverse City North Stars during the club's inaugural 2005–06 season before accepting a position as associate coach of the OHL's Erie Otters.

He accepted a position to become the new assistant coach for the Syracuse Crunch of the AHL, the 2010-11 American Hockey League season.