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.
In January 1999, he attracted the attention of Northwich Victoria's manager Mark Gardiner but a proposed loan move was thwarted by Bailey sustaining a minor hamstring injury.
[6] Bailey continued to attract the attention of Northwich Victoria's manager Mark Gardiner and having turned down one offer to join the Vics to remain at the Giant Axe, Gardiner came back with an improved pay offer which coupled with the lure of moving nearer to home in the Stoke area proved too much for Bailey and he departed Lancaster City in January 2000.
[10] He debuted for the club in the 3–1 victory at Leyton Orient on 7 August 2004 and was an ever-present member of the side until he sustained a peroneal tendon tear[11] in the 1–1 home draw with Cambridge United on 19 October 2004.