1926 and 1932, he played Minor Counties Championship cricket for Berkshire. He also played football and hockey. In January 1930 Dempsey was admitted to the Staff College, Camberley, graduating in December 1931. His fellow students in the Junior Division included numerous future general officers, including William Gott, George Hopkinson, George Symes, Maurice Chilton, Walter Mallaby, Stuart Rawlins and John Nichols. The Senior Division attending from 1929 to 1930 included Neil Ritchie, Herbert Lumsden, George Erskine, Ivor Hughes, Reginald Denning, Harold Redman and Ian Playfair, while in Dempsey's second year, the Junior Division, attending from 1931 to 1932, included Brian Horrocks, Sidney Kirkman, Frank Simpson, Joseph Baillon, Arthur Dowler, Thomas Rees, Keith Arbuthnott and Cameron Nicholson. The instructors in Dempsey's first year included Henry Maitland Wilson and Trafford Leigh-Mallory. Boy Browning was the college adjutant. Nearly all of these men were to achieve high rank in the upcoming war. 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. Completion of the course at Camberley was normally followed by a staff posting to allow the graduate to practise his skills, and Dempsey's first posting after Camberley was as a General Staff Officer Grade 3 (GSO3) on the staff of the Military Secretary, Major-General Sidney Clive. Dempsey was responsible for the careers and assignments of all officers below the rank of colonel, with access to their annual confidential reports. Dempsey, who was promoted to major on 22 September 1932, held this post until late January 1934, when he handed over to Horrocks upon receiving an appointment as brigade major of the 5th Infantry Brigade. The brigade, commanded by Brigadier Victor Fortune (Francis Nosworthy from 1935), formed part of the 2nd Division, then commanded by Major-General Archibald Wavell. It was serving in Aldershot Command and took part in numerous large-scale military manoeuvres throughout Dempsey's time as brigade major. After handing over again to