Aston Manor, Birmingham born outside left Clarence Gregory began his football career with Wellington Town in 1919 and came to the attention of First Division Sunderland, who signed him in the summer of 1920, his Football League debut, and only appearance for The Wearsiders, coming in a 0-0 draw at Tottenham Hotspur in April 1921. After a further season in the reserves at Roker Park he was released and joined Third Division (South) Queen’s Park Rangers in the 1922 close season,
In the 1922-23 season Gregory played in all of Rangers’ games through to Christmas Day, scoring in a 2-0 win over Norwich City in September, but then lost his place, playing only 3 more matches in March and early April. After 24 appearances for Rangers he moved to non league Yeovil & Petters United in the summer of 1923, before returning to Wellington Town a year later. In 1925 he joined Hereford United, and finished his career with spells at Leamington Town in 1926 and Rugby Town in 1927.