Despite a ruptured kidney causing him to miss all but one match in 2000,[1] Medhurst comfortably won the Bernie Naylor Medal in 2001 for the most goals in the league.
[3] Medhurst made a successful debut in round 1, 2002 in a Western Derby against the West Coast Eagles, kicking three goals and earning an AFL Rising Star nomination.
The following six weeks saw Medhurst struggle to hold his place in the Collingwood outfit, a number of low-possession efforts in the seniors forcing the former Docker to play with Williamstown in the Victorian Football League (VFL).
Although the Magpies lost to Geelong the following week in the preliminary final by a five points, Medhurst's three goals helped keep his team in the contest.
[3] Medhurst was selected in the 2008 All-Australian team as a forward pocket and finished runner-up in Collingwood's 2008 best-and-fairest award.
On the 23 September 2012, Medhurst played in Claremont's premiership victory over East Fremantle in the 2012 WAFL Grand Final.