Simmons started out with his home side, Blackwell Colliery. In 1908 he transferred to Sheffield United. He was a member of the Sheffield United team who won the FA Cup final in 1915. The Manchester Guardian stated that he was the most attractive player on the pitch and his quick attacks, which he mixed between runs down the wing and through the centre, left the Chelsea defence standing. He scored the first goal of the match just before half time when he half volleyed a cross into the top corner of the net.