Leeds Rhinos Bailey made his
Super League début for Leeds in 2002 at age 18. Bailey played for the
Leeds Rhinos as a 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. In the final against
Australia Bailey played from the interchange bench in the Lions' 44–4 loss. As
Super League IX champions, the Leeds club faced
2004 NRL season premiers, the
Canterbury-Bankstown Bulldogs in the
2005 World Club Challenge. Bailey played as a in Leeds' 39–32 victory. He played for Leeds in the
2005 Challenge Cup Final as a in their loss against
Hull FC. Bailey played for the
Leeds club as a in their
2005 Super League Grand Final loss against
Bradford. Bailey played in the
2008 Super League Grand Final victory over
St Helens. Bailey played in the
2009 Super League Grand Final victory over
St. Helens at
Old Trafford. Bailey played in the
2010 Challenge Cup Final defeat by
Warrington at
Wembley Stadium. Bailey played from the interchange bench for Leeds in the
2011 Challenge Cup Final defeat by the
Wigan at
Wembley Stadium. Bailey played in the
2011 Super League Grand Final victory over
St. Helens at
Old Trafford. Bailey played in the
2012 Challenge Cup Final defeat by
Warrington at
Wembley Stadium. Bailey played in the
2012 Super League Grand Final victory over
Warringtonat
Old Trafford. On 8 May 2014, he made his 300th career appearance for the Leeds club. Bailey played in the
2014 Challenge Cup Final victory over the
Castleford Tigers at
Wembley Stadium.
Hull KR In 2015 Bailey moved to
Hull Kingston Rovers. He was not fit enough to play his former club
Leeds in the opening game of the season but went on to score on his début the week after. In March it was announced Bailey had been released because of personal issues after only playing one game for the club.
Castleford Tigers A month later he joined the
Castleford Tigers for the remainder of the season where he rejoined former coach
Daryl Powell. He played six games and scored one try before being released at the end of the season.
Warrington Wolves In November 2015
Warrington announced the signing of Bailey on a one-year contract for the 2016 season. There, he would play under
Tony Smith again with whom he won two Grand Finals with at Leeds. Bailey publicly opened up about his struggle with depression in 2016. He played in the
2016 Challenge Cup Final defeat by
Hull F.C. at
Wembley Stadium. He played in the
2016 Super League Grand Final defeat by
Wigan at
Old Trafford.
Toronto Wolfpack Ahead of the
2017 season, Bailey signed for newcomers to Rugby League
Toronto. He made his début for the new club in an 80-0 victory over
North Wales Crusaders. 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. It was later reported that the players had twice missed curfew during the trip.
Workington Town After his departure from Toronto, Bailey joined league 1 side Workington in January 2018. After playing just six games for the Cumbrian team, Bailey was offered a chance to move up to the Championship to play for Leigh and left Workington in April 2018.
Leigh Centurions and retirement Bailey joined Leigh in April 2018 and made 11 appearances for the club in the
2018 season. In November 2018, Bailey joined
Featherstone Rovers on a trial contract but decided to retire from the game in February 2019 aged 35. ==Controversies==