 Bailey began his career as a trainee with his home town club Stoke City before moving to Rochdale on a free transfer in October 1996.He made his Football League debut for the club in the 1–0 away victory over Torquay United on 3 December 1996 and by the end of March had secured a regular birth in the first team.The 1997–98 season saw Bailey maintain his presence in the team, making 24 league starts with a further nine appearances from the substitutes bench.