 Bailey made his Barnet debut against Farnborough Town in a 0–0 draw in the Football Conference on 17 August 2004, and scored his first goal for the club on 4 September 2004 in a 5–1 win against Morecambe.He helped the club to promotion in the 2004–05 season and then establish itself in Football League Two over the following two years.In 2006-7 he was voted Barnet FC Player of the Season by the club's supporters.