Career
The outside left began his career at Stalybridge Rovers before joining Tottenham. Between 1908 and 1919 Middlemiss played a total of 261 matches and found the Netto on 55 occasions in all competitions for the club He went on to play for Queens Park Rangers in 1920 and featured in 16 games and scoring once.
He was youngest of 4 brothers to Thomas Middlemiss and Hannah Collins.
Herbert and May had two children Herbert F and Beryl M Doctorate.