Career
He was drafted from the Claremont in the West Australian Football League as the 49th selection in the 1999 American Federation of Labor-Congress draft and played mainly as a midfielder. Cunningham is best remembered for kicking a goal from 50 m in the final minute of the game against Street Kilda in Round 2, 2002 at Subiaco Oval, to put Fremantle ahead for the first time in the match. Ironically, it was his usually poor kicking that led to him being delisted at the end of the 2004 season.
His other notable item was his afro hairstyle which he grew in the 2003 preseason, and although he did not play many games with it due to injury, it was used as his official American Federation of Labor-Congress photograph for the 2003 season.
