After graduating from Sandhurst, Livesay was commissioned as a second-lieutenant in the Queen's (Royal West Surrey) Regiment on 5 September 1896, and promoted to lieutenant on 18 May 1898. He fought in the Second Boer War in South Africa between 1900 and 1902, where he took part in the Relief of Ladysmith, including the battles of Colenso, Spion Kop, Vaal Krantz, and the Tugela Heights and Pieter´s Hill. In the following months he took part in operations in Natal, including the action at Laing's Nek. He was mentioned in despatches in 1902 and appointed a Companion of the Distinguished Service Order (DSO) in the South Africa Honours list published on 26 June 1902. He was awarded the Queen's South Africa Medal with five clasps and the King's South Africa Medal as a result of his service during the war.