Singh joined the Royal Air Force College Cranwell at the age of 19 and graduated in 1939. He joined the No. 1 Squadron IAF and served in the North-West Frontier Province. In World War II, he commanded this squadron during the Arakan Campaign and was awarded the Distinguished Flying Cross. In 1945, he attended the RAF Staff College, Bracknell. After the Partition of India in 1947, he led the first fly-past of Royal Indian Air Force (RIAF) aircraft over the Red Fort in Delhi. He then commanded Air Force Station, Ambala at the rank of Group Captain. In 1950, after completing the staff course at Joint Service Defence College, Latimer, Buckinghamshire, he was promoted to the rank of Air Commodore and took over the Operational Command. He commanded the Operational Command in two stints. In 1958, the post was upgraded to Air Officer Commanding-in-Chief at the rank of Air Vice Marshal.