Born in Boldon Colliery[1] Middleton began his career at North Shields where he attracted the attentions of Chesterfield who signed him for £50.
[2] He established himself as first choice keeper but saw his career interrupted by World War II, remaining in the area to work as a miner during the conflict.
[2] Off the pitch Middleton ran a grocer shop in Old Whittington and became involved in local Labour Party politics, even becoming the only active Football League player to serve as a Justice of the Peace.
[2] The Spireites' relegation in 1951 saw him leave the club to move to top-flight Derby County, where he made 115 appearances.
He began promisingly with a 2–1 win over Accrington Stanley although his record proved mediocre and after a 5–1 defeat at Doncaster Rovers in October 1959 he left the club.