He is the younger brother of former New South Wales and Australia representative forward Phil Bailey.

Bailey made his NRL début for the Newcastle Knights against Wests Tigers at Campbelltown Stadium in round 10 of 2006.

[10][11] He played five-eighth for the Sea Eagles in their 2009 World Club Challenge win over the 2008 Super League Grand Final winners, the Leeds Rhinos.

The injury ravaged Sea Eagles failed to advance past the first week of the finals in both 2009 and 2010 and the emergence of young New Zealand five-eighth Kieran Foran in 2009 saw Bailey released by the club at the end of the 2010 season (ironically Manly, with most of its star players free from injury, would go on to win the 2011 NRL Grand Final with Foran at 5/8).

After leaving Manly, Bailey joined Super League club London Broncos on a three-year deal from the 2011 season.