 In June 2004, Macclesfield Town's manager Brian Horton announced that the club had agreed terms to sign Bailey with Bailey signing a one-year contract with the club following the end of his contract with Lincoln City.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 in the 1–1 home draw with Cambridge United on 19 October 2004.The injury would keep Bailey out of action until the 2–0 away defeat to Swansea City on 25 March 2005 but after that he remained in the first team picture for the remainder of the season as Macclesfield reached the play-offs, losing out to his former club Lincoln City in the semi-finals.