[2][3] After education at Eton and Trinity College, Cambridge, John Christopher Willoughby became in 1879 a lieutenant in the 3rd Battalion Oxford Light Infantry.
[2] He served in the Egyptian campaign in 1882 (awarded medal with clasp, and bronze star), in the Nile expedition in 1884–1885 (mentioned in despatches), and with the British South Africa Company's Force in Matabeleland in 1893.
In South Africa in the Second Boer War from 1899 to 1900 he was present with Cavalry Headquarter Staff during the siege of Ladysmith and at the relief of Mafeking was appointed major, under General Hunter, in charge of Transport of Flying Column (mentioned in despatches and awarded a medal).
[2] He was ultimately major in command of the 1st Motor Battery of the Army Service Corps before his death aged 59 in April 1918.
The Jameson raiders skirmished against Boer resistance on 1 January and the next day were defeated and surrendered after losing approximately 30 men.