Sheffield born right half Harry Bentley played local football for Heeley Friends and captained Sheffield Boys in 1905 in their fixture with London Boys in the inaugural English Schools’ Football Association championship in 1905, and received a glowing profile the following year in the Yorkshire Telegraph & Star highlighting his “fine turn of speed” and claiming that “it is not a reckless prophecy to suggest that he will, before many years have elapsed, be appearing in distinguished company, for he has all the attributes of a successful player”.
Signing for Sheffield Wednesday in April 1909 as an 18 year old but didn’t make his Football League debut until April 1914 at Oldham Athletic. In November, The Star Green ‘Un commented that despite Wednesday’s history of sound recruitment, they might not have realised how good Bentley would become. Coming into the side because of injury to the long-serving Tom Brittleton he retained the right half position even after Brittleton’s return to fitness, having “continued to play a very clever, brainy game. He tackles well, and, what’s more, makes it his business to place the ball where it will be of advantage to his forwards.” He was a first team regular in 1914-15, however the onset of the First World War forced the suspension of peacetime football and Bentley lost four seasons and saw service in The Royal Field Artillery before resuming his career with Wednesday in 1919.
However he only played 17 matches in their first post-war season and was sold to Brighton & Hove Albion for £250 in August 1920 after 3 goals in 52 matches. Two seasons on the South coast saw him clock up 70 appearances for The Seagulls, before he moved to Swindon Town for £350 in the 1922 close season, although at Swindon he was barely used, clocking up only 11 matches over the next two seasons before moving back to Yorkshire non league football in 1924 with Maltby Main.