Chilton established himself as a centre half in Matt Busby's first post-war team and helped United to triumph in the 1947–48 FA Cup and was a key member of the 1951–52 league championship winning team. He was made club captain during the 1953–54 season. Having missed just 13 games in nine seasons at United and with 175 consecutive appearances to his name, Chilton requested a rest from first team action in early 1955. He was replaced by Mark Jones, one of the rising Busby Babes, and never returned to first team action.