Having started his career at Scotswood FC, the main part of Harry's career would be spend at Chesterfield where he would play 121 games.

His impressive form would see him move to Newcastle United for £8.5k. And whilst Leicester City tried to sign the player during the following season Harry would stay at Newcastle until 1938.

The number of games he could play for the Magpies was curtailed by the way and he eventually move to Grimsby Town.