Robert Woollcombe was born in London in 1922 and educated at Marlborough College. He enlisted in the 60th Rifles in 1941, and was commissioned into the 6th Battalion, the King's Own Scottish Borderers in 1942, with whom he served in North-West Europe. He served with the 2nd KOSB in India from 1945-46. He association with the Regiment spanned three generations: his uncle was killed in action with the KOSB in France in 1914, and his grandfather became Colonel of the Regiment and commanded IV Army Corps which bore much of the brunt of the Battle of Cambrai in 1917. Until his death in 1996, Robert Woollcombe lived in West Sussex.