 Bailey joined Gloucester Rugby from Bristol Rugby in 2004, having scored 14 tries in 21 matches for Bristol in the 2003–04 season.He played 49 matches for Gloucester Rugby and scored 11 tries.One of the most memorable tries that he scored was against London Wasps in May 2006 when James Simpson-Daniel ran rings around Lawrence Dallaglio and passed the ball to Bailey who rounded off a beautiful try.