The Football Association in the autumn of 1899 gave 100 guineas to the funds for widow, orphans and families of soldiers serving in what became known as the Second Boer War and for those maimed and wounded. They recommended that on 2 December 1899 – “Football Saturday” – clubs belonging to the Association should donate a minimum 10% of gate receipts on that day. Clubs unable to do this on the 2 December were encouraged to fix a date on the nearest possible Saturday. In Leicester alone between £80 and £90 per week was required to relieve the wives and families of those reservists left destitute by the recalling of their husbands “to the colour.” It is not known how much was raised in Leicestershire, but Harborough contributed £3 2s to the War Fund as the result of a collection made on the field and a share of the gate.

Black Week (10-17 December 1899) took place just a few days later when the British suffered three devastating defeats in the Second Boer War at the battles of StormbergMagersfontein and Colenso. In total, 2,776 British soldiers were killed, wounded and captured during this period. Included in that number was Mr. D. D. Stewart, (private , Scots Guards, died 13.12.1899) a former secretary of St. Mary’s Victor FC. His name along with the other 300 plus Leicestershire soldiers who died in the conflict are inscribed in the Roll of Honour on bronze panels attached to a granite plinth of the Grade II Leicester South African (Boer) War memorial (designed by Joseph Crosland McClure of Leicester Art School.) situated on the corner of the Town Hall Square, Leicester, at the junction of Every Street and Horsefair Street. Funded by local subscription it was unveiled on 1 July 1909 by Field Marshall Lord Grenfell.

The Second Boer War lasted from 11 October 1899 until 31 May 1902. In the war, the British Empire fought against the Afrikaans-speaking Dutch settlers of two independent Boer republics, the South African Republic (Transvaal Republic) and the Orange Free State. Winston Churchill, who later became famous, was captured but escaped. At this time, the British made use of concentration camps. This weakened the Boers. It helped the British stop the war from lasting any longer. The British troops won the war. As a result, both republics were annexed to the British Empire. Later, both were eventually incorporated into the Union of South Africa, a dominion of the British Empire, in 1910. The 1st Battalion of the Leicestershire Regiment served in South Africa throughout the conflict helping to defend Ladysmith (1899-1900) before joining the campaign in the Orange Free State.