Headland played junior football for Karrinyup Junior Football Club. His school football was for Lockridge Senior High School where he played alongside future AFL players Garth Taylor, Brett Johnson and Dwayne Simpson. In 1997 Headland represented Western Australia (WA) at the under 16 national championships and won the best and fairest medal and was selected in the All-Australian team. In 1998 he represented WA in the AFL Under 18 Championships, made his league debut for Subiaco Football Club and won both the WAFL rising star and the Subiaco best and fairest award. He also toured Ireland with the AFL/AIS Academy side.