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.
In June 2004, Macclesfield Town's manager Brian Horton announced that they had agreed to sign Bailey, who signed a one-year contract after his Lincoln City deal expired. He made his debut for the club in a 3–1 win against Leyton Orient on August 7th, 2004, and was a regular player until he suffered a peroneal tendon tear during a 1–1 draw with Cambridge United on October 19th, 2004.