O'Grady first played for the Montreal Garnets until 1913, before joining the Montreal Wanderers from the National Hockey Association . He remained loyal to them for three years until 1916. After the defender had spent the 1916/17 season with the Montreal Stars, the Wanderers brought him back to their squad for the start of the National Hockey League for the 1917/18 season. There he played four games for the team that immediately had to stop playing because their venue had fallen victim to a fire. O'Grady then ended his career.