On 17 June 2022, he became head of recruitment at Fleetwood Town Born in Salford, Greater Manchester, Riley started his career at Bolton Wanderers since he was seven and attended Walkden High School.
[11] Before the 2013–14 season, Riley returned to the first team in the pre-season friendly match against Skelmersdale and things became worse for him when he damaged his anterior cruciate ligament, which kept him out for ten months.
[17] On 14 January 2015, Riley completed a free transfer to Bury,[18] in a deal that included a sell-on clause in Bolton's favour.
[19] Because of a hamstring injury sustained in training, his debut was delayed until 27 January, when he came on as a substitute for Kelvin Etuhu in the second half in a 1–0 loss against Accrington Stanley.
[21] After serving a three-match ban,[22] he returned to the side and scored the only goal against Shrewsbury Town to confirm the club's qualification to the play-offs.
Riley moved to fellow League One side Shrewsbury Town in July 2016 for an undisclosed fee, signing a two-year deal.
[29] Following surgery and subsequent recovery from his broken leg, Riley returned to the side in an EFL Trophy group stage match against Coventry City on 29 August 2017.