Born in Newcastle-upon-Tyne,[1] Bailey began his career at Newcastle United, captaining the under-23 team.[2] Bailey suffered from injuries which saw him out-of-action for 538 days.[2][3] After being released by Newcastle, he played in non-league with Gateshead,[4] before signing for Doncaster Rovers in June 2023, having trialled with the club in 2021.[5][6][7]