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.
[1][2] Headland only played 3 games for Brisbane in 1999, making his debut in round 13 against Sydney, in which he scored 2 goals.
Poor form in the last few rounds saw him dropped for the finals series, and he missed the Brisbane Lions first premiership.
He would play all remaining games that year, and in a 15-game purple patch from round 11 to the end of the year he would kick 30 goals, average 21 possessions and poll 16 Brownlow Medal votes, including three best-on-grounds and votes in six consecutive games.
In the lead up to the 2003 AFL season Headland was chosen in an ATSIC Chairman's All-Star team that played Carlton at Marrara Oval, Darwin.
In Round 4, 2003, Headland was one of 7 indigenous players to represent Fremantle, the most ever to play in a single AFL team.
The other indigenous players for Fremantle that day were Troy Cook, Jeff Farmer, Antoni Grover, Roger Hayden, Steven Koops and Dion Woods.
[7][8] Headland was selected in July 2013 as a candidate for the Palmer United Party for the Federal seat of Durack.
Headland announced his candidacy only one day after he had told a West Australian paper that "I've had one conversation which has sparked a bit of interest...