Playing games against all the great professional sides of the era, Oakley was an assured defender whose peak years for the club were the 1898/99 season and the 1899/1900 season, during which he rarely missed a match.
Playing games against prominent professional sides of the era, Oakley served as a reliable defender whose most productive years were in the 1898/99 and 1899/1900 seasons, during which he consistently participated in matches.