Willie O'Grady was raised in Limerick, the middle child of three brothers. Known by the nickname "Buddy", O'Grady was a mainstay on his hometown team in the League of Ireland, Limerick FC, along with his younger brother, Gerry, having first appeared in the 1946-47 season. In 1948, O'Grady was the only player selected from his club to travel to London and play on the Irish Olympic football team, which lost its only match to Holland by a score of 3-1.
He later returned to Limerick and was a member of the League of Ireland Shield winning squad of 1953, continuing to play until the 1954-55 season. He emigrated to England shortly thereafter where he continued to reside until his death in 1985.