Stackpole made his VFL debut in 1935 with Collingwood and played as a reserve in that year's winning Grand Final as well as their premiership triumph the following season. Due to the success of Collingwood the competition for a place in the side was tough and as a result he left the club for Fitzroy during the 1939 VFL season. Stackpole formed a strong partnership with fellow Fitzroy rover Allan Ruthven and his last game of football was their 1944 Grand Final win in which he kicked 2 goals.