Newcastle born outside left Bert Middlemiss began his career at Stalybridge Rovers in 1906 before joining Stockport County, spending 1907-08 at Edgeley Park without making a first team appearance for The Hatters. He then signed for Second Division Tottenham Hotspur, for whom he made his Football League debut against Wolverhampton Wanderers in September 1908, becoming a regular fixture in the first eleven straight away. He was an ever present, scoring 13 goals in the club’s promotion campaign when they finished Second Division runners up, a career best goals total, he twice managed double figures again in 1911-12 and 1912-13, when he was again an ever present.
Between 1908 and 1919 Middlemiss played a total of 261 matches and found the net on 53 occasions in all competitions for the club, but the First World War effectively ended his Spurs career and he was limited to only four post War appearances. He joined Queens Park Rangers in the summer of 1920 and featured in 16 games during the rest of 1920, scoring once, before retiring in 1921.