Sheffield United and Wolves were but two of a number of decent sides which passed up the chance of signing the young Ray Middleton. He joined the Spireites from North Shields in October 1937 for fifty quid, turning professional just after his eighteenth birthday. Ray spent a year in the shadow of Jack Moody before making his debut after two games of the '38-9 season. His coolness, fine judgement and quiet confidence in his own ability saw to it that he remained a fixture in the side until being sold to Derby upon the Spireites' relegation to Division Three (North) in 1952. At 5'9" and 10st 6lb, he was quite small for a 'keeper, even by the standards of the day, but he was a robust chap and was, apparently, adept at clattering opposing players to the deck when jumping for the ball. Ray stayed locally during the war and worked down the mines, famously insuring his hands for £2,000.
He was the lynch-pin of an excellent defence just after the war, forming understandings with the likes of Billy Kidd, the Milburn brothers and Freddie Capel. It was recognised that Chesterfield had perhaps the meanest defence outside Division One at the time, and only the club's careless habit of selling quality forwards denied it a place in the top flight.
Ray was called upon to play for the England 'B' side four times, touring with them to Italy in 1950, and played at that level with team-mate Stan Milburn. Off the field, he began to look to the future by taking a grocer's shop in New Whittington, and became active in local politics. In 1950, Ray became a justice of the peace, and remains the only active professional footballer to have become a magistrate. Having settled well into Chesterfield life, then, he was forced to undertake a substantial reappraisal of his future when the club were relegated. A 'keeper of his class would have been out of place in the Third Division: he recognised that, so did Chesterfield and so did Derby County. He enjoyed mixed fortunes at the Baseball Ground, playing in the First Division, but suffering relegation to Division Two in 1953.He was freed at the age of 34 and joined Boston United as player/manager. This move scuppered his plans to stand as a Labour candidate in the 1954 Chesterfield borough elections.
Ray enjoyed one more day of glory at Boston. Having assembled a fine side with a liberal sprinkling of former Derby players, he took the Pilgrims to the Baseball Ground in the 1955-6 FA Cup.In one of the game's greatest giantkilling feats, Boston came away having won 6-2.Hartlepools United appointed him to their Secretary/managership in 1957 and he stayed for two years, without much success; he returned to Boston and remained as their Secretary until his untimely death in 1977, at the age of 58.
For Chesterfield: 250 Football League appearances. 72 clean sheets, 306 conceded.