A Richmond junior, Pickering played for Auckland, and had a New Zealand national rugby league team trial in 1992 however was not selected.[3] He played for Fiji at the 1992 Pacific Cup.[4]
He made his first grade début for Workington Town in the 1992/93 English season in the old division 3 competition. He helped Town into second place behind Keighley Cougars, and to the final of the Divisional Premiership competition, when they were narrowly beaten by Featherstone Rovers, from the division above.
In 1993–94, Pickering was the driving force behind Workington Town doing the Division Two and Premiership double as they won the league in emphatic style, and beat London Crusaders at Old Trafford 30–22.
Back in the game's elite, Workington enjoyed an impressive 1994-95 campaign finishing ninth out of 16 and reaching the quarter-finals of the Challenge Cup. Once again, Pickering was the side's shining light with even the finest prop forwards in the game struggling to come to terms with the Fijian's swashbuckling style of play.
He then spent three seasons with the Canterbury Bulldogs, playing in nine first grade matches before a horrid run of injuries practically ended his career.
Pickering then spent a season each at Sydney City and Castleford Tigers before returning to the Canterbury Bulldogs for the 2000 season.[5][6][7]