Biddulph, Staffordshire born full back Jimmy Oakes played junior football for Milton Albion in 1922 from where he joined Second Division Port Vale, turning professional in November 1923 and making his Football League debut against Southampton in March 1924. He became a first team regular from October 1924 and although Port Vale were relegated in 1928-29, he played 36 times in the following campaign at The Valiants won the 1930 Third Division (North) Championship to return to the Second Division at the first time of asking.
He was sold on to Second Division Charlton Athletic for £3,000 in January 1933 after 3 goals in 307 appearances for Vale, and although he couldn’t help save Charlton from relegation at the end of season, he played 37 times as The Addicks won the Third Division (South) Championship in 1934-35, so adding Oakes to a select band of players who won both versions of the Third Division title. The following season he was again a regular in the Charlton line up as they won back to back promotions, finishing as Second Division runners up to enter the top flight for the first time in the club’s history. He continued to play in the First Division until the abandonment of peacetime football in September 1939 on the outbreak of the Second World War, by when he had made 236 appearances for Charlton, but the War forced his retirement from football in a career spanning over 500 games.