Sergeant Sidney Redgrave joined the 48th Highlanders in 1937. When war was declared he enlisted with the 1st Battalion, 48th Highlanders in September 1939 and went overseas with the battalion on the Reina del Pacifico in December 1939. While in England Sid was transferred to Divisional Headquarters for the General Staff reading aerial photographs and decoding and recording messages. He returned to the battalion for transport to the landings at Pachino, Sicily. Sid served in Sicily, Italy and Holland being one of the few Highlanders who served the entire period of combat with the battalion. Returning to Toronto with the battalion on 1 October 1945, was discharged and married Isobel that month.
In his civilian role, before and after the war, Sid was with CCM Ltd. (Canadian Cycle Manufacturers)