Undrafted, Stapleton played for two seasons with the Green Bay Gamblers of the USHL. Stapleton then represented the University of Minnesota Duluth for four seasons, where he led the team in scoring as a freshman and had back-to-back 40 point seasons.\n', '

After a brief stint with the Portland Pirates of the AHL, he signed with Jokerit of the Finnish SM-liiga, completing a tryout which led to a one-year contract. During his first Jokerit season, Stapleton won the SM-liiga silver medal and finished second in playoff scoring.\n', '

On June 6, 2008, Stapleton signed as a free agent to the Toronto Maple Leafs for the 2008–09 season. Stapleton was assigned to the Toronto Marlies of the American Hockey League on September 26, 2008.\n', '

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