Private T. Caroline served with the 1st Battalion during the Boer War of 1899-1902 and was with “A” Coy. He was the batman/groom to Major Gen Smith Dorrien throughout the campaign. On the 29th May 1901, he was wounded at Vlakfontein, South African and was wounded again on the 30th September 1901 at Moedwil.  

Private Caroline was transferred to Aldershot South Africa WEF on the 1st January 1901 and was with “F” Coy. He transferred from pay of 1st K.S.G Infantry WEF on the 1.9.1901. On the 1st September 1902, Private Caroline transferred to the South African Army Reserve WEF