[7] Bailey played for the Leeds Rhinos as a prop in their 2004 Super League Grand Final victory against the Bradford Bulls.

He was then selected in the Great Britain team to compete in the end of season 2004 Rugby League Tri-Nations tournament.

[8] Bailey played for the Leeds club as a prop in their 2005 Super League Grand Final loss against Bradford.

[11][12] Bailey played from the interchange bench for Leeds in the 2011 Challenge Cup Final defeat by the Wigan at Wembley Stadium.

[citation needed] A month later he joined the Castleford Tigers for the remainder of the season where he rejoined former coach Daryl Powell.

He then went on to play in seven more games that year and helped in securing the Wolfpack's Kingston Press League 1 triumph and subsequent promotion to the Betfred Championship.

On 18 January 2018, it was reported that Bailey, along with teammates Fuifui Moimoi and David Taylor, parted ways with the club by "mutual agreement" following a preseason training camp in Portugal.

[32] In November 2018, Bailey joined Featherstone Rovers on a trial contract but decided to retire from the game in February 2019 aged 35.

[35] Bailey played for the Leeds Rhinos as a prop in their 2004 Super League Grand Final victory against the Bradford Bulls.

On 23 December 2004 the Rugby Football League fined Bailey along with Leeds' teammate Keith Senior £1,500 each after they tested positive to the banned stimulant ephedrine.

[36] Bailey was charged with "evading, refusing or failing to submit to sample collection" during a routine drug testing session at Toronto's Lamport Stadium on 30 May 2017.