 Sunderland had been unable to gain a place in the inaugural season of the Football League and played friendly matches in the 1888–89 season, Dickson scoring four goals in nine appearances.In 1889 he joined Football League side Aston Villa and did well for the Birmingham-based club scoring 34 goals in 64 matches and earned a FA Cup runners-up medal in 1892 FA Cup Final .He joined fellow Midlands based club Stoke in time for the 1892–93 season where he scored 11 goals as Stoke enjoyed their best season in the league up to that point.