Enjoying his time at the Staff College, Dempsey captained the college cricket team. He also excelled at equitation, beating Gott in the point-to-point competition. Students worked in syndicates; Dempsey's chose to study the August 1914 Battle of Gumbinnen. They toured the battlefield with "Hauptmann" Anton Reichard von Mauchenheim genannt Bechtolsheim, a German Army officer who had been on two months' secondment to the British Army in 1930. The syndicate noted the influence that poor communications had on the outcome of the battle, and speculated as to how armoured fighting vehicles might have been employed had they existed at the time.