Shackleton was a second round draft selection by Collingwood, on the back of his Morrish Medal winning performances with the Tassie Mariners in the 2002 TAC Cup season.
[1] He played at Williamstown in 2003, the feeder club for Collingwood which compete in the Victorian Football League.
The following year he made his AFL debut, against Richmond on the Melbourne Cricket Ground.
[3] Delisted without playing another game, Shackleton joined the Tasmanian Devils in 2005.
[4] He later returned to his original club, the Burnie Dockers, whom he would captain in the 2011 Tasmanian Football League season.