Cowdenbeath, Fife born wing half Billy Simpson played junior football for Donibristle Colliery in 1923, Cowdenbeath YMCA in 1924, Fulford White Rose in 1925, Dunbar United in 1926 and Musselburgh Bruntonians in 1927 before joining Scottish League Clyde in 1928. He was then signed by First Division Aston Villa in 1931 and made his Football League debut against Chelsea in January 1932, but during his four seasons at Villa Park he was mainly a fringe player, scoring once, in a heavy defeat at Blackpool in March 1933 in 29 appearances before returning to Scotland in 1935 to join hometown club Cowdenbeath.
But he soon returned to the Midlands joining Northampton Town in the summer of 1936 where he was an ever present in 1936-37 making 44 appearances. He moved again, however, at the end of the season, this time to Walsall, where he played until the outbreak of the Second World War, scoring 6 times in 79 appearances for The Saddlers. After the War he joined non league Bromsgrove Rovers in 1945.