Enlisted on 15th August 1938. His flying training was unsuccessful. He moved on to air navigation at which he excelled passing out in Class A with 84.8%. He finished his training at No. 7 Elementary & Reserve Flying School Desford at the end of November 1938. He moved to Acklington with No. 2 A.O.S. Squadron to practice dropping bombs and learn to be an observer. On completion of his training in1939, he joined 21 Squadron based at Eastchurch. His log book at the time (signed by Fl. Lt. L. V. E. Petley) recorded that he was flying Blenheim L1355. In February 1940 he was flying to Norway Sweden and Finland attacking German patrol vessels. He bombed enemy troops in France during May and June 1940 and provided air support for the evacuation from Dunkirk. He was then posted in July 1940 to 13 OTU Bicester, probably training navigators. His aircraft crashed on take off on 26th November 1940.
He returned to the front line on 30th April 1941 when he was posted to 107 Squadron based at Leuchars in Scotland. His pilot was Laurence Petley. The Squadron moved to Great Massingham east of Kings Lynn in Norfolk on 12th May 1941. The Squadron flew the longer range Blenheim 1Vs. The missions were hazardous. Most raids were made in daylight at low level to avoid radar often without fighter escort.
When Germany turned its attention to Russia it was decided that the Group should make deep penetration raids into Europe by day to pull enemy fighters away from the Eastern Front. On 27th June 10 crews from 105 Squadron and 10 from 107 Squadron were briefed to carry out a low level attack on the Docks at Bremen which meant flying over the German mainland for 105 miles. W. Cdr. Petley with Ray on board led the formation which was unsuccessful due to a large enemy convoy being in the docks. The element of surprise was lost and the mission was aborted. Petley took the blame and the Squadron was posted to Driffield in Yorkshire. 107 Squadron was then scheduled to target Bremen on 4th July 1941 led by Wg. Cdr. Petley with F/L. R. A. Bailey and gunner Sgt W. M. Harris on board. They were shot down by flak in the target area. The raid itself was hailed as a great success and Ray was awarded a posthumous D.F.C. in the London Gazette on 13th March 1942 with effect from July 4th 1941 for carrying out a difficult reconnaissance operation in the face of enemy fighter opposition in April 1941 "He proved himself an inspiration to all by his coolness and keenness" (Evening Star 14.3.1942)