As a junior, he captained the Western Australian Under 18s team in the 2000 national championships and played for the East Perth Football Club in the WAFL, including their 2001 premiership team.
Webster's playing career was plagued by injury, having three knee reconstructions in four years. He first injured his left knee during the first game of the Under 18s carnival and had to undergo a knee reconstruction which put him out of the remainder of the 2000 season. In 2002, after showing promising form in the pre-season games for Fremantle, he suffered another injury to the left knee requiring a second knee reconstruction in a practice match against Collingwood at Fremantle Oval. A week after being one of Fremantle's best players in its first ever final in 2003, he damaged his right anterior cruciate ligament playing for East Perth in the WAFL preliminary final. He returned to the AFL for Round 21, 2004 and played the last two games of the season. 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.
After the end of his playing career, Webster took on a role as a development coach at the Carlton Football Club. In 2013, he additionally took on the role of senior coach of Carlton's VFL-affiliate, the Northern Blues.[1]
After the 2015 season Webster was released by Carlton. He then signed as a Development coach with the West Coast Eagles in October.[2]