Glasfurd was commissioned as a second lieutenant in the 2nd Battalion, Argyll and Sutherland Highlanders on 21 October 1893, and was promoted to lieutenant on 23 February 1896. He served as adjutant of the 1st Battalion from 4 May 1898, including during their stay in South Africa during the Second Boer War. Promoted to captain on 11 January 1900, he saw action in the Orange Free State; the battle of Paardeberg (February 1900), where he was wounded; the Transvaal and the Orange River Colony where he was seriously wounded near Rustenburg in October 1900.