He primarily served during the Second World War during which, however, he did not see much active service on account of a long bout of illness during his only posting in the conflict-zone, in Myanmar from 1944.

At the time of his death on 16 April 2024, he was the oldest living pilot of the Indian Air Force at the age of 103.

[1][2] His grandfather was Sundar Singh Majithia, making him first cousin once removed of the artist Amrita Sher-Gil.

After retirement from the Air Force, he settled at his family's estate in Sardarnagar, near Gorakhpur in Uttar Pradesh.

[11] On 18 February 1947, Dalip Singh married Joan Sanders at his family's estate in Gorakhpur, whom he had met during his service in Melbourne, Australia.

She was in the Women's Royal Australian Naval Service as a code breaker during the war, working in the Fleet Radio Unit, Melbourne.