General Sir Miles served in both World Wars. During the Second World War he had a close relationship with Bernard Montgomery and commanded XIII Corps for the invasions of Sicily and Italy and later commanded the British Second Army during the Battle of Normandy and made notably rapid advances in the subsequent campaign in Northern France and Belgium. He was the first British Army commander to cross the Rhine.
Sir Miles was educated at Shrewsbury where he captained the first XI Cricket in 1914. After the Royal Military Academy, Sandhurst he joined the Royal Berkshire Regiment and won an MC during service on the Western Front. Between the wars he played two first-class cricket matches for Sussex against Oxford University and Northamptonshire. For 5 or 6 years he played Minor Counties Championship cricket for Berkshire.
Military historian Carlo D'Este wrote of him as follows:
"A career infantryman, Dempsey was an ardent student of military history and during the interwar period had frequently visited Europe to study its battlefields firsthand. Blessed with an active and incisive mind, a phenomenal memory and a unique skill in reading maps, Dempsey would soon leave his army staff in awe over his ability to remember everything he saw on a map, to bring a landscape literally to life in his mind even though he had never actually seen it. This talent proved particularly important during the crucial battles around Caen in June and July 1944. Dempsey was considered the Eighth Army's best expert in combined operations and, as he grew in experience, Montgomery soon recognized his potential for army command. The two men shared many qualities, including a disdain for paperwork and a determination, based on their First World War experiences, never to waste their soldiers' lives."