Boulding's goals attracted interest from a number of clubs including League One side Cheltenham Town, and League Two teams Bradford City, former club Grimsby Town, Lincoln City and Rotherham United. Boulding and his brother were expected to sign for Cheltenham Town but had a change of heart and instead moved to League Two side Bradford City in July 2008, joining the team on their tour of Scotland. Boulding was one of four Bradford players to make his debut on the opening day of the 2008–09 season against Notts County. He was a second half subtitute replacing fellow striker Barry Conlon, as Bradford won 2–1. His first goal for City came in their third game of the season to open the scoring in a 2–0 victory against Rochdale on 23 August 2008, which put them second in the table.