Although Roy was born in the Bathurst district of NSW, his family were living at Howell near Inverell before World War 1. Roy was twenty-two when he enlisted in Sydney in February 1918, giving his occupation as Baker and next of kin his father, William Henry Winter of Howell.
Roy joined the Heavy Artillery Group 36, Reinforcement 18 and sailed from Sydney for England on RMS Orontes in June 1918. After a few weeks training he was sent to France in November 1918 where he was a Gunner with the 2nd Siege Battery. Roy returned to Australia and was discharged in January 1920. He died in Sydney in 1977.