[3] He captained the Sheffield Boys football team that faced London Schools in the inaugural English Schools' Football Association (ESFA) championship in 1905,[4] 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.
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.
"[7] He made 34 appearances out of a possible 41 in 1914–15,[8] at the end of which competitive football closed down for the duration of the First World War.
[6] Bentley then signed for Brighton & Hove Albion, newly admitted to the Football League, and club historian Tim Carder wrote that "his experience was invaluable" to a struggling team.
[5] He made 64 appearances over two years, either at full back or wing half, and moved on to another Third Division South club, Swindon Town, for a £350 fee – £100 more than Brighton had paid for his services.