Pickering was born in Manchester and began his career with non-league Buxton before becoming a professional with Rotherham United.
He spent five seasons at Millmoor making 111 appearances scoring twice helping the side gain promotion in 1991–92.
He earned a move to Premier League side Coventry City in October 1993 and was a regular for two seasons at Highfield Road making 75 appearances.
[1] New Stoke manager Brian Little deemed him to surplus to requirements at the start of the 1998–99 campaign and he joined Burnley.
[1] After a season at Turf Moor Pickering went on to play for Altrincham, Chesterfield and made seven appearances for Chester City.