Nicknamed "Cocky", Bennett started his career with his home town club of Mexborough, where his form prompted Sheffield United to try and sign him on a number of occasions although both he and his father held out for a better deal.

[1] Initially supporters felt Bennett had a surly attitude and was not fit enough to play at the top level as he was a heavy, thick-set man.

Dropping two stones following a fitness regime, however, he showed a good turn of speed and became a mainstay of the Blades side that dominated the game in that period.

[1] Despite his success Bennett was placed on the transfer list in 1903 but persuaded United to give him a new contract and stayed with the South Yorkshire club until 1905, when he moved to Bristol City.

Bennett was killed in April 1908 following a roof fall at the Denaby Main Colliery[1] as he was making his way back to the surface after his shift, leaving a widow and four children.