Cummings was born to Doctor and Mrs. H. L. Cummings in Franklin, Tasmania, Australia on 13 April 1896. He had a brother, Roy, who would serve in the Australian Flying Corps with him. Cummings enlisted in the 2nd Signal Company, Australian Imperial Force on 27 October 1914, giving his profession as cart driver and claiming 15 months prior service in C Company, 93rd Regiment of the militia. He embarked for departure from Australia in December 1914; he was in the 15th Battalion as a bugler. He served in the Gallipoli Campaign before transferring to aviation.
Cummings was assigned to train at the flying school at RAF Shawbury. He completed all phases of his training in three weeks, and was posted to No. 2 Squadron AFC. Although he had yet to score an aerial victory, his rise through the ranks was rapid, and he was appointed Flight Commander on 17 October 1916. He subsequently liaised with Rene Fonck in operations against Manfred von Richthofen's Flying Circus. Details of Cummings' service over the next year and a half are missing. By May 1918, however, he was assigned to 2 Squadron AFC as a Royal Aircraft Factory SE.5a pilot. On 3 May 1918, he scored his first aerial victory. His brother Roy mailed home a copy of orders describing the action; this was reprinted in The Mercury in the Cummings' native Tasmania. The reprint gives a vivid description of early aerial warfare: "Lieutenant E. D. Cummings...attacked a...triplane, and fired a burst from both guns into it. The enemy aircraft immediately went down in a spin, followed by Lieutenant Cummings, still firing. The enemy aircraft then turned on its back, and finally crashed....At this point Lieutenant Cummings was attacked by four...triplanes, who shot away his elevator controls, instrument board, petrol and oil tanks; his machine went down almost out of control, but he managed to keep it out of a spin until it...crashed. His safety-belt broke, and he was thrown clear of the machine into a shell-hole...." Nothing daunted, Cummings went on to score eight more confirmed aerial wins and rise to the rank of captain. His bravery would win him a Distinguished Flying Cross, which would be gazetted on 8 February 1919:
List of aerial victories
Between the wars
Cummings returned to Australia after the war; on 28 August 1919 he flew an aerobatic exhibition in a Sopwith Pup over downtown Hobart, including eight loops. The exhibition was a public relations stunt to draw a crowd to subscribe to a Peace Loan of 750,000 Pounds to care for military veterans. After his departure from Hobart, he barnstormed locally for the Peace Loan, despite engine trouble after departing Launceston for Longford and Devonport on 9 September 1919. On 11 February 1920 Cummings was invested with the Distinguished Flying Cross by General William Birdwood in Cummings' home town of Franklin. On 7 June 1923 Cummings was granted a short service commission in the Royal Air Force as a Flying Officer. On 7 June 1928 he was transferred to Class A Reserve of the Royal Air Force; he would remain in the reserves in various capacities until World War II. While Cummings was a reservist he was promoted to Flight Lieutenant on 4 February 1931. Also during this time, on 27 April 1932, he was elected to membership in the Royal Aero Club.