Lt Baillie enlisted in the 2nd Battalion, 48th Highlanders in 1940 for training. He joined the 1st Battalion in England in May 1943 and was appointed to command the Mortar Platoon of Support Company. When the battalion prepared to sail for the landings in Sicily in July Lt Baillie became a Platoon Commander in Baker Company. In Sicily he was wounded July 21/22 in the ambush at the crossroads after the battle to take Assoro and was sent to hospital. He returned to the battalion remaining until December 1943 when the battalion was at the Arielli River and was one of three officers returned to England under Exercise Pouch for additional training. Baillie did not return to the battalion after training but was reassigned.