After school, Winston completed a Bachelor of Economics at the University of Sydney and then went to work at Joyce Biscuit Ltd. He enlisted in the Royal Australian Air Force in 1940 and was stationed in England. In 1942, he was a casualty of war in Germany. He is remembered on the OKGA War Memorial.
His brother Alan (OKG40) and his cousins also attended the School.
War Service
1940-1942 - Royal Australian Air Force 402243, Flying Officer, 150 Squadron RAF