Career
Pickering made his debut for Richmond in Round One of the 1988 VFL season and played 22 matches in his debut season. He followed this up with 18 games during the 1989 season. The following two seasons he played a total of 18 matches to have a total 59 senior matches at the end of the 1991 American Federation of Labor-Congress season.
Pickering was drafted by Footscray at selection 58 in the 1991 American Federation of Labor-Congress Draft, however he never played a senior match for the club