As a corps the most prominent appearance of the Cape Town Highlanders in despatches was in connection with a mishap for which, however, they were in no way to blame. It will be remembered that in October 1900 the enemy, having been beaten in the Transvaal, made a great effort all over the Orange River Colony, attacking or sneaking into various towns. In Lord Roberts' despatch of 15th November 1900, after referring to the attempts on Jagersfontein, Fauresmith, and Philippolis, he said: "Again at Jacobsdal on 25th October the treacherous part played by some of the inhabitants in admitting the Boers into their houses during the night led to the temporary occupation of that town. The Boers opened fire at daybreak on the garrison, and 14 men were killed and 13 wounded, nearly all belonging to the Cape Town Highlanders and Cape Artillery. On the news reaching the Modder River Post, troops were at once detached to Jacobsdal and drove the Boers off. The houses of the treacherous inhabitants were destroyed; in three of them were found large stores of soft-nosed bullets. In this engagement the Boer commandant, Boshman, was killed". Many of the defenders were shot at close range in their tents or as they were rushing out. Unfortunately the tents were on the market square, practically surrounded by houses to which the enemy had got access and from which they were able to fire in comparative safety. As the attack commenced at 4.30 AM and continued till 2.30 PM, it was most creditable to the garrison, numbering in all under 60, that they did not surrender. Eight dead Boers were found. The relieving force was a very small party of Cape Police, Cape Town Highlanders, and Cape Garrison Artillery, about 50 in all. As the Boers were nearly 300 strong, they evidently took the relieving party for the advanced guard of a stronger body.
Throughout 1901 detachments of the Cape Town Highlanders were garrisoning Ookiep and other places ill Namaqualand, and although the enemy made sundry attempts none of these places fell into his hands. In his telegram of 21st April 1902 Lord Kitchener said: "In west bulk of enemy's force is round Ookiep, which has been attacked unsuccessfully. Reinforcements have arrived now". The defenders of Ookiep were afterwards congratulated on what was a most creditable stand. They held out against repeated attacks from 3rd April to 4th May. Lord Kitchener said in his despatch of 1st June, "No details of the defence of the town have as yet been received, but General French is of opinion that Colonel Shelton and his men offered a gallant and determined resistance to the many unsuccessful attempts made to capture the position". The garrison consisted chiefly of the Namaqualand Town Guard, small detachments of the 5th Royal Warwickshire Militia Regiment, of the Cape Garrison Artillery, the Namaqualand Border Scouts, and a few Volunteers.
The Mentions gained by the corps were as follows:—
LORD ROBERTS' DESPATCHES: 31st March 1900.—Captain H Watermeyer, who acted as aide-de-camp to Lord Roberts.
2nd April 1901.—Captain Watermeyer, for performing various duties loyally and well. Private T Moore, since killed.
LORD KITCHENER'S DESPATCH: 23rd June 1902.—Lieutenant Colonel W Standford; Captains W A Hare, J D Dell; Quartermaster Sergeant W Clark; Company Sergeant Major P Hardy; Sergeant C Penthill.