The 2nd Battalion sailed on the Lismore Castle and Harlech Castle about 19th October 1899, and got to Durban about 14th November. Along with the 2nd Queen's, 2nd Devon, and 2nd West Yorkshire, they formed the 2nd Brigade under Major General H Hildyard. The work of the brigade is sketched under 2nd Queen's.

At Willow Grange, 22nd November, the East Surrey supported the West Yorks in the assault, and in his report, dated 24th November, General Hildyard said, "The behaviour of all ranks of the 2nd East Surrey Regiment when engaged was satisfactory under great difficulties". At Colenso the battalion was not so heavily engaged as the 2nd Queen's and Devons. The battalion's losses were 1 killed and 31 wounded.

At Venter's Spruit the battalion had heavy fighting on the 21st January, and lost 1 officer wounded and 5 men killed and about 25 wounded.

At Vaal Krantz they were the centre of the crest line on the 7th February, and lost 2 men killed and 12 wounded.

During the fourteen days between 13th and 27th February they were, like the rest of the brigade, constantly fighting. On the 22nd, when we were knocking our heads against the strong defences east of Grobelar's, "the East Surrey were ordered forward to reinforce the 60th Rifles; and they helped them with such spirit to maintain the passive strife—the business, you might say, of using the flesh of men to resist the bullets of the enemy—that they were praised afterwards by the general and thanked by the 60th Rifles". That day Lieutenant Colonel Harris "received ten separate wounds". Corporal A E Curtis for his efforts to assist the colonel gained the VC, and Private Moreton for helping Curtis got the distinguished conduct medal.

On the 23rd the battalion had a bad time, losing very heavily.

In the final assault on 27th February the East Surrey worked along with and to the right of the 1st Rifle Brigade, these regiments being the first line of attack on what was perhaps the most strongly fortified part of the position. The work was handsomely done.

During the fourteen days the battalion's losses were approximately 1 officer and 27 men killed, 6 officers and 86 men wounded.

Colonel Harris, 7 other officers, and 15 men were mentioned in despatches for work in the relief operations, 3 of the men getting the distinguished conduct medal.

At Alleman's Nek on 11th June the East Surreys formed with the Queen's the first line in the attack on the left hill. There again all went well.

The battalion's losses were approximately 3 men killed, 1 officer and 6 men wounded. Three officers were mentioned in General Buller's despatch as to the turning of Laing's Nek, and 6 officers and 4 non-commissioned officers and men were mentioned in that general's final despatch of 9th November 1900.

The brigade moved along the Natal-Pretoria Railway, and was afterwards largely occupied in garrison and column work along the line.

In Lord Roberts' final despatches 12 officers and 15 non-commissioned officers and men were mentioned.

In 1901 part of the battalion was in Colonel Colville's column and part in Colonel Eimington's, and they did a lot of hard marching in the south of the Transvaal and the north of the Orange River Colony.

One officer and 3 men gained mention in Lord Kitchener's despatches during the war, and in his final despatch 3 officers and 3 non-commissioned officers were named.

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