Bailey was originally a junior of the Shellharbour Sharks club before signing for the Illawarra Steelers as a teenager prior to their joint venture with the St. George Dragons in 1999.

[2] After debuting in 2000 he went on to make a further one hundred and nineteen appearances for St. George Illawarra before becoming newly formed National Rugby League franchise Gold Coast Titans' second signing for their inaugural 2007 season.

[3] His talent was quickly noticed and while still an adolescent was signed to a junior development deal with Australian Rugby League club the Illawarra Steelers.

After playing a sole season of lower grade rugby league with St. George Illawarra, Bailey had impressed the club's top tier coaches enough to earn a spot on the bench for the Dragons' 2000 NRL season opener against local rivals the Cronulla-Sutherland Sharks;[5] a game they would eventually lose twenty-eight to twelve.

The beginning of the 2002 season saw Bailey recover fully from the injury that had prematurely ended his previous playing year and while he missed all of the club's trials including the Charity Shield fixture against South Sydney he made his return to the team for their opening round clash against Cronulla-Sutherland and would go on to appear in a further twenty consecutive appearances putting in several man of the match performances and along the way earning himself a call up to the New South Wales State of Origin side.

Further injury at the completion of the year ruled Bailey out of the Australian national side for their end of season Northern Hemisphere tour after he required surgery to fix a damaged ear.

[11] After missing the Australian tour and having his first full off-season of training under his belt since 2002 meant that Bailey would play in St. George's trial matches that year including their 34 – 8 victory in Charity Shield against South Sydney.

Bailey earned his second international cap when he was selected to play for Australia from the interchange benh in the 2004 ANZAC Test match against the Kiwis but not make another appearance for a few years.

He eventually made his return during the final series but not even his presence could help St. George Illawarra from narrowly losing to the Penrith Panthers.

On 23 June 2005; it was announced that the newly formed Gold Coast Titans club was chasing the signature of Bailey for its inaugural 2007 season.

Bailey was selected to play for the Australian national team from the interchange bench in the 2007 ANZAC Test match victory against New Zealand.

[21] After playing in the Titans' last few matches of the 2010 NRL season with a broken thumb, Bailey was awarded the Paul Broughton Medal for the club's player of the year again.