Biddulph, Staffordshire born left back Jimmy Oakes played junior football for Bethesda Mission and Milton Albion from where he joined Second Division Port Vale in 1922, 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 was selected to play for The Rest against The English Team in an international trial match at The Hawthorns, West Bromwich Albion, on 3rd January 1928, although he didn’t receive a call up to the England squad.
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 managed a rare feat in scoring from his own half in a 2-1 defeat to Stockport County at The Old Recreation Ground on Christmas Day 1929, albeit with help from the wind.
He was sold on to Second Division Charlton Athletic for £3,000 in January 1933, where he became club captain, after 3 goals in 307 appearances for Vale. With The Addicks he became the first player to play for the opposing club in a re-arranged match. He played for Charlton in their 2-1 home win over Vale after the original fixture was abandoned on the previous Boxing Day, 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 then skippered Charlton Athletic to their highest ever League finish when they finished runners up in the League Championship to Manchester City in 1936-37. 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, and Oakes guested for Port Vale in March 1940, and later for Stoke City, but the War forced his retirement from football in a career spanning over 500 games.