After half a season with the Barrie Colts in 1998-99, Bootland was acquired by the Toronto St. Michaels Majors where he went on to play parts of four seasons with the club tallying 263 points (127-136-263) throughout his career. In the summer of 2002 the Detroit Red Wings signed the Schomberg, Ontario native as a free-agent and in his first season with the organization he split his time between the AHLs Grand Rapids Griffins and the ECHLs Toledo Storm.

In 2003-04, Bootland made his NHL debut with Detroit and went to split his season between the Red Wings and their AHL affiliate in Grand Rapids. He would continue to toil in the AHL over three seasons and see limited action with the Red Wings before he was signed as a free agent in the summer of 2007 by the New York Islanders.

After appearing in only four games with the Islanders, and 28 games with their AHL affiliate in Bridgeport, Bootland was traded to the Anaheim Ducks in exchange for Matt Keith.

Courtesy of the Hockey Hall of Fame