 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.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.