During December 1899, Jacobsdal was an outlying town of Lord Methuen's advance northwards, along the Cape Town-Kimberley railway.  After their severe loss at Magersfontein, the British withdrew, back along the railway line, to regroup. Jacobsdal was an outlying town during the Western Front.

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By January 1900, Lord Roberts had taken over command of the South African campaign. His blitzkrieg march, from  the Orange River Station (near Hopetown) took the British forces directly to Bloemfontein, in a north-easterly direction. Once again, Jacobsdal felt the ripples of this advance, as commando's, columns and medical services moved through the town.

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But in October 1900, Jacobsdal became the direct focus of attack. General JBM Hertzog and Capt HPJ (Hendrik) Pretorius surrounded Jacobsdal on the night of 25 October, killing 14 British troops on the market square. These soldiers belonged to the Cape Town Highlanders and the Cape Garrison Artillery, who were responsible for guarding Jacobsdal. The British were very bitter about the collusion of local residents with the Boer forces. In Lord Roberts’ despatch of 15 November 1900, he described how the Highlanders were shot at close range in the market square, in their tents or as they were rushing out. Nevertheless, the Highlanders stood their ground for 10 hours until they were relieved by additional forces from Modder River. “The houses of the treacherous inhabitants were destroyed", wrote Lord Roberts in his report.