The 2nd Battalion sailed on the Britannic about 7th January 1900, arriving about the 27th. Along with the 2nd South Wales Borderers, 1st East Lancashire, and 2nd North Staffordshire, they formed the 15th Brigade under Major General A G Wavell, and part of the VIIth Division under Lieutenant General Tucker. For the general work of the division see notes under 2nd Norfolk Regiment.
The Cheshires had no very serious fighting on the way from Modder River to Bloemfontein.
In the action at Karee Siding on 29th March the infantry employed was the VIIth Division, and this battalion was said to have done well. They had about 22 wounded.
At the Zand River the battalion was sent forward on the evening of the 9th May to seize and hold a drift. This they successfully accomplished, and the brigade crossed early on the 10th, clearing the enemy from strong positions north of the river.
After the occupation of Johannesburg the 15th Brigade was detailed to garrison the town, and the Cheshire Regiment long remained in that vicinity.
Eight officers and 12 non-commissioned officers and men were mentioned in Lord Roberts' final despatch.
On 5th December 1900 the battalion relieved the 2nd Royal Scots Fusiliers as garrison of Frederickstad. In January 1901 part of the battalion was holding a post on the line south of Johannesburg when the enemy attacked fiercely. The attack was very gallantly driven off.
In 1901 the battalion furnished the infantry of columns under Sir H Rawlinson, Colonel E C Williams, Colonel Hickie, and other commanders, which did much arduous but useful work in the South-West Transvaal. Three officers, 1 non-commissioned officer, and 1 private were mentioned by Lord Kitchener for good work during the later phases of the war. In the final despatch 5 officers and 4 non-commissioned officers were mentioned.