Oakes played for Bethesda Mission and Milton Albion before joining Port Vale as an amateur in August 1923, signing as a professional in November.

[1] 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.

[1] Oakes made 36 appearances in the 1929–30 season as Vale finished top of the Third Division North, playing alongside Billy Wootton, George Shenton, and Bill Cope in a solid and consistent defence.

[1] Oakes and Shenton formed a formidable partnership in 1930–31, as Vale posted the highest league finish in the history of the club; he played 41 games, scoring one goal.

[1] He played 12 games in 1932–33 before he was sold to Charlton Athletic for £3,000 in January 1933, with Port Vale desperately needed the funds.

He played for Charlton in their 2–1 home win over Vale after the original fixture was abandoned on the previous Boxing day.