Following in his father's footsteps, Mike Stapleton was selected by the Blackhawks in the 1984 Entry Draft and played with the OHL's Cornwall Royals for three seasons, (his father, Pat, played ten seasons in the NHL for the Bruins and Blackhawks). He played for team Canada at the World Junior Championships where he won a silver medal.
The 1986-87 season saw Stapleton play with the Canadian National Team until making his NHL debut with Chicago. That year also marked his first action in the Stanley Cup playoffs. For the next four seasons with the Hawks, Stapleton spent the majority of his playing time in the minors until signing with the Penguins as a free agent in 1992. The team had just come off back-to-back championships but had trouble reclaiming its glory the next season.
The Oilers claimed Stapleton off waivers during the 1993-94 season, and it was there he stayed for the rest of the year and the next season. His next stop was Winnipeg when he signed as a free agent with the Jets in 1995. When the team moved to Phoenix in 1996, Stapleton followed for the next three seasons before being claimed by Atlanta in the Expansion Draft of 1999.
His next stop was New York as Stapleton signed with the Islanders in 2000 as a free agent. However, he finished the year in Vancouver when he was dealt to the Canucks.