Educated at Felsted School and Bedford School, Huddleston was commissioned into the Coldstream Guards in 1898, and then served in the Second Boer War. He took part in operations in the Orange Free State from April to May 1900, then served in the Transvaal May and June 1900, including actions near Johannesburg, and at the Battle of Diamond Hill. During the war he transferred to the Dorsetshire Regiment as Second lieutenant 26 May 1900, and was promoted to Lieutenant on 19 November 1901.
He was mentioned in despatches for actions in December 1901 ("for dash and leading … which lead to captures", dated 25 April 1902).
He also served in World War I and then became General Officer Commanding Sudan in 1924. He was appointed Commander 14th Infantry Brigade in 1930 and then joined Eastern Command in India in 1934.
He became Commander for the Baluchistan District in Western Command of India in 1935. He was appointed Lieutenant Governor and Secretary of the Royal Hospital Chelsea and was then briefly General Officer Commanding Northern Ireland District from April to July 1940 before being appointed Governor General of Anglo-Egyptian Sudan later that year.
He retired from that post in the face of considerable local criticism in 1947.