Oakes started his senior football career in England with Wolverhampton Wanderers in 1935 signed by Major Frank Buckley.
He scored twice, one being a terrific 13th-minute dribble and drive and the other a penalty, as Blackburn Rovers defeated Bolton Wanderers 4–0 on 1 November 1947.
In total Oakes played 35 leagues and two FA Cup games for Blackburn Rovers scoring 9 goals.
Playing alongside many Blackburn Rovers stalwarts, his best-known teammate was probably the England full-back, Bill Eckersley.
[3] Oakes joined Manchester City at the start of the season 1948–49, where he lined up alongside Joe Fagan and also two highly distinguished goalkeepers in Frank Swift and Bert Trautmann.
Cup that season Manchester City were defeated in the third round by Everton, now the club of Dumfries born forward Jimmy McIntosh.
On 23 February 1952 a staggering crowd of 26,552 squeezed very tightly in to see Queens play in a Scottish Cup third round 3–1 win for Hearts.
Sir Alex Ferguson recalled this match recently by saying "The other reason I remember that game was due to the average age of the Queen of the South forward line, which was probably about 34, with Black, Broadis, Patterson, Dunlop, and Oakes playing.
Shortly after in February 1960, Oakes was joined on the playing staff by another ex-opponent from his days in England's top division, goalkeeper George Farm.
Twenty three years after his debut, Oakes played at Queens until the age of 40 in 1960, clocking up a total of 457 games for the club.
Oakes is fourth highest in the club's record appearances list behind Allan Ball and Iain McChesney and in between team-mates Jim Patterson and Dougie Sharpe.
With the exception of his last season in Dumfries, Oakes time as a Queens player was spent in Scotland's top flight.