Arbroath, Angus born outside left Tommy Dilly started with hometown clubs Arbroath North End and Arbroath in 1899 and played for Heart of Midlothian in a trial friendly at Arbroath in May 1900, but he wasn’t taken on to the Tynecastle playing staff. He also played for the County of Forfarshire in 1900. He continued to impress and in November 1902 signed for First Division Everton, making his Football League debut at Sunderland the same month. But opportunities were very limited at Goodison Park and having scored a brace of goals at Newcastle United in January 1906, his only goals for The Toffees in 9 appearances, he joined Second Division club West Bromwich Albion in March 1906.
He was part of their 1907 FA Cup run that saw them eventually beaten 2-1 by former club Everton in the FA Cup semi final at Burnden Park, Bolton. But he fell out of favour at The Hawthorns from the start of the following season and played only once for Albion in the new 1907-08 season, scoring both goals as The Baggies beat Gainsborough Trinity 2-1 in October 1907, and the same week he transferred to Derby County after 10 goals in 37 appearances for The Albion, scoring on his Derby debut against Leeds City the next weekend. But he wasn’t retained and after 2 goals in 10 appearances for The Rams he joined Bradford Park Avenue in June 1908, where he appeared only twice the following season. He joined Birmingham & District League club Walsall in 1909, playing for Shrewsbury Town in 1910, Worcester City in 1911 and Kidderminster Harriers in 1914 before his eventual retirement.