Tommy Simpson was born in Dundee in 1904. He played junior football for Dundee Osborne before signing for Dundee United in December 1923. He became a regular in the side, and made a major contribution to their promotion to the Scottish First Division in 1924–25.
After more than 100 appearances in league and cup competition over three-and-a-half seasons, he left for Brighton & Hove Albion for a £250 fee. He played 30 times in the Third Division South in 1926-28 scoring 6 goals the before returning to Scotland where he joined Montrose.