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 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 In July 2003, he was found guilty of brawling in the street in