He started his career at hometown club Washington United before transferring to Barnsley sometime prior to 1910. He played in both FA Cup finals that Barnsley reached, in 1910 and 1912. In the first Barnsley lost in the replay to Newcastle United. The second also went to a replay but Barnsley won, defeating West Bromwich Albion by one goal in extra time. The "Manchester Guardian" praised his play in the first match, and in the replay Glendenning won the ball from a West Brom player and passed it to Harry Tufnell to score in the last minutes of extra time.