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James McGregor (SN 1859), born at Hay NSW, was a single 25 year old engineer at the time of his enlistment in Liverpool, NSW on February 10th 1915. His unit embarked from Sydney on board the Shropshire in March. He arrived at Gallipoli at the end of May where he was wounded in action at the Battle of Lone Pine, suffering a gunshot wound to his head. He was being evacuated to hospital on board the Dunluce Castle when he died of his wounds on August 8th 1915 and was buried at sea. With no known grave his name is listed on the Australian Memorial at Lone Pine, Gallipoli.
His brothers William, Rob Roy and Stanley also served in the AIF and are each honoured with a tree in the Avenue.