Bailey made his first grade debut for Manly Warringah in Round 5 1999 against South Sydney.

At the end of 1999, Manly merged with arch rivals North Sydney to form the now defunct Northern Eagles side.

Bailey made 19 appearances for Cronulla in his first season at the club as they reached the preliminary final against New Zealand but were defeated 16-10.

[4] At the end of the 2003 NRL season, Bailey went on the 2003 Kangaroo tour of Great Britain and France, helping Australia to victory over The Lions in what, as of 2025, is the last time the two nations contested an Ashes series.

He made his Wigan Warriors, Super League début in a 10–16 defeat by Warrington Wolves at the JJB Stadium on 9 February 2007.