Bootland was drafted 252nd overall in the 2000 NHL Entry Draft by the Colorado Avalanche from the Toronto St. Michael\'s Majors of the Ontario Hockey League. After his final year in the OHL, Bootland signed with the Detroit Red Wings as a free agent to a three-year contract on August 29, 2002.\n', '

Bootland made his NHL debut with the Red Wings in the 2003–04 season, recording two points (1–1–2) and 74 PIM in 22 games. Bootland spent the next three years with the Red Wings affiliate, the Grand Rapids Griffins of the AHL before getting recalled by the Red Wings on March 5, 2007, playing in six games.\n', '

On July 6, 2007, Bootland signed with the New York Islanders. He appeared in four games with the Islanders before he was traded to the Anaheim Ducks in exchange for Matt Keith on January 9, 2008.\n', '

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