Norwich City signed 18 year old midfielder Regan Riley from Bolton Wanderers on 1st February 2021 for a fee of £250,000. He had joined the Bolton academy at the age of 9 and made one first team appearance for Wanderers, in a 5-0 League One loss to Tranmere Rovers in August 2019. He also appeared for them in the EFL Trophy.

He struggled with inuries during 2021/22 meaning his game time was limited. Regan has wonderful attributes for a central midfielder, including his energetic engine to cover large areas of the pitch, while also his technical quality makes him an attacking threat.

He was released by Norwich on 20th May 2024. 

On 13th September 2024 he signed for National League North side Radcliffe on a one year deal.