Tom Cunningham played as a goalkeeper for Sunderland Juniors before signing for Leeds City in August 1908 as reserve to Tom Naisby and Harry Bromage.

With two such fine keepers around, opportunities were rare for Cunningham; he only made one appearance in the first-team, as a last-minute replacement for Naisby for the game at Derby in January 1909. The match was something of a nightmare for Cunningham, ending in a 5-1 defeat.

When the promising young Tony Hogg was signed in April 1909, Cunningham saw the writing on the wall and left Elland Road at the end of the season, never playing professionally again.