Tynemouth, Northumberland born full back James Oakley began his football career with Seaton Delaval in 1920 and played for Blyth Spartans in 1921 before joining First Division Sunderland, making his Football League debut at Bolton Wanderers in September 1922, his only first team appearance in his debut season. Throughout his 8 seasons at Roker Park he was always on the fringes of the first team but never a regular, often playing second fiddle in a strong squad boasting the likes of Warney Cresswell. As a result his best return was in the 1924-25 season when he played in 20 first team games.
Nonetheless he accumulated 90 first team appearances for The Wearsiders before he joined Second Division Reading in 1930, however the move was not a success and he played only 10 games in their relegation season, and was released in the summer of 1931. He joined Northampton Town and although he only played 4 times for the first team in 1931-32, he came into the team the following season and made 29 more appearances before joining non league Kettering in 1933, staying a season there before joining Birtley in 1934, where he finished his playing career.