Charles Sheppard was born in Ballarat, Victoria, was single and a Plumber when he enlisted with the 2nd Field Company Engineers as a Sergeant on 1 September 1914 at the age of 25. His unit embarked from Melbourne, Victoria, on board Transport A3 Orvieto on 21 October 1914. He was diagnosed with dysentery and a gunshot wound to the right toe and foot and was admitted to a series of hospitals before being embarking overseas to Alexandria for base duties, receiving a temporary appointment to Company Quartermaster Sergeant. On 3 July 1916 it was taken on strength that he joined with the 2nd Division Engineer HQ . On 18 November 1916 he was promoted to 2nd Lieutenant and to full Lieutenant on 8 March 1917.

On 1 June 1918 he received a severe gunshot wound to the left leg, resulting in its amputation, marking the end of his military career. He returned to Australia aboard the D14 on 25 June 1918. He also enlisted to serve during WW2 with service number V148316.

His brother Albert also served in the AIF and was awarded the Distinguished Conduct Medal and is honoured with a tree in the Avenue.