After spending time with Barnsley's Shadow Scholarship program, he signed a contract and joined their academy in October 2020.[3] He signed a one-year contract extension with the club on July 3, 2021.[4]
On July 11 Simpson was loaned to Danish 1st Division club Esbjerg fB on a half-season deal until December 31.[5] However, only two months later, on September 8, 2021, the club confirmed that he had signed a permanent deal until June 2024 with Esbjerg.[6] He left the club in the summer of 2024 at the end of his contract.[7]
On transfer deadline day, August 30, 2024, Simpson moved to Danish 2nd Division side AB.[8] He left the club again on 6 July 2025.[9]
