He was drafted to the Fremantle Football Club as the first selection in the 2001 AFL Rookie Draft, and was elevated to the senior list during the 2003 season following an outstanding year for East Perth, which included being awarded the Simpson Medal as the best player for Western Australia in the state game against South Australia.
After being in and out of the Fremantle team for the next 3 years, Webster injured his left knee again early in the 2008 season whilst playing for East Perth.
Webster underwent a knee reconstruction via the controversial LARS method of using a synthetic ligament instead of the body's own tissue with a view to an earlier than anticipated return in season 2008.
Webster's brother Ryan, father Ron and grandfather Ray also all played league football for East Perth.
Ron Webster, who died in January 2006, was also the CEO of the Western Australian Amateur Football League.