The 1st Battalion left Suez on 28th November 1899. On arriving in South Africa about 14th December it was sent to assist Sir W Gatacre, who had just suffered his reverse at Stormberg (see 2nd Northumberland Fusiliers). Shortly after landing the battalion was sent to Sterkstroom, and afterwards it held Bushmanshoek, and they remained in this district until after the advance on Bloemfontein compelled the Boers in the colony to slacken their hold, and so allowed General Gatacre to move north to Burghersdorp and Bethulie. In this advance the enemy was seen, but his bullets were seldom felt except at and about the crossing of the Orange River. There seems to be no doubt that the road bridge over the river was saved by the gallantry of Lieutenant Popham and some of the Derbyshire Regiment. Under a heavy fire these brave men rushed on to the bridge and cut the wires which were intended to fire the mines set for blowing up the bridge.

When several new brigades were being born in March and April 1900, the 21st, composed of the 1st Sussex, 1st Derbyshire, 1st Camerons, and City Imperial Volunteers, was brought into existence under Bruce Hamilton. The work of the brigade is sketched under the 1st Sussex. The 21st Brigade was, along with the 19th, put under General Ian Hamilton, to be a part of the army of the right flank, and some account of their advance is given under the Duke of Cornwall's Light Infantry.

In the many actions on the right flank between 3rd and 24th May 1900 the 21st Brigade and its commander did well, and the Sherwood Foresters soon added to their reputation. While at Florida or Doornkop, fought on 29th May, after Ian Hamilton's force had become the army of the left flank, the battalion bore a distinguished part. An account of the action is given under the 1st Gordons, who made the assault. At Diamond Hill this battalion did good work. The 21st Brigade was engaged in the operations which culminated in Prinsloo's surrender, but the Derbyshire Regiment had not such severe fighting as some other battalions, being engaged on convoy work a good part of the time. De Wet, it will be remembered, broke out on 16th July with 1600 men. Broadwood went in pursuit, and finding the Foresters escorting a convoy on the Lindley road, he snapped them up to assist in doing some trekking after the fleet and ever-fleeing Boer. On 5th August De Wet was still practically surrounded south of the Vaal, but on the 7th he crossed the river, broke out, and eventually escaped.

In Lord Roberts' final despatches of 2nd April and 4th September 1901, 16 officers and 18 non-commissioned officers and men of the battalion were mentioned.

During the latter part of 1900 and early months of 1901 the battalion did much marching, but it was not till 28th May 1901 that any good opportunity for gaining distinction came. On that date Colonel Dixon was moving about near Vlakfontein, north-west of Krugersdorp, in difficult country; his force being,— Left, under Major Chance: 2 guns of 28th Battery, 1 pom-pom, 230 Imperial Yeomanry, one company Derbyshire Regiment. Centre: 2 guns 8th Battery, 1 howitzer, two companies King's Own Scottish Borderers, one company Derbyshire. Right: 2 guns 8th Battery, 200 Scottish Horse, two companies King's Own Scottish Borderers. Under cover of a grass-fire the enemy broke the screen of the left column, driving in the Yeomanry and seizing the two guns. Things were looking hopeless, but the infantry rose to the occasion, and by a charge which is unsurpassed by any similar feat in the history of the war the men of the Derbyshire Regiment recaptured the guns, but at a terrible cost,—18 of their number being killed and about 70 wounded. Other troops assisted the Foresters, but to them belongs the glory of a magnificent achievement.

Two officers and 6 men were mentioned by Lord Kitchener in his despatches for gallantry at Vlakfontein. The number appears few, but where practically every man belonging to the two companies present displayed absolutely unsurpassable gallantry it must have been difficult to select names. The cause of mention in the case of Colour Sergeant Henod is worth quoting, the circumstances being so unusual. "After being taken prisoner, exhibited great courage and coolness in removing our wounded from bursting of our shells". This looks worthy of the coveted cross.

On 30th September 1901 the same column, now under Kekewich, was again fiercely attacked at Moedwill in the Megaliesberg range. The words of Lord Kitchener's despatch of 8th October may be given: "At dawn on the following morning his camp was heavily attacked by a force of at least 1000 Boers under Generals Delarey and Kemp, who had evidently followed up our column from the valley of the Toelani. The attack, which lasted from 4.45 am till 6.45 am, being delivered upon three sides of our camp with great vigour and a lavish expenditure of ammunition, was quickly repulsed after severe fighting, in which all ranks displayed great gallantry, the conduct of the 1st Battalion Derbyshire Regiment being especially distinguished. The enemy, foiled in their attempt to rush the position, were compelled to fall back, and they apparently retired in a northerly and northwesterly direction. Our losses in this action were severe, 1 officer and 31 men being killed, and 26 officers, including Colonel Kekewich, and 127 men wounded. To give some idea of the severity of the fire to which the troops were subjected, it may be mentioned that three picquets were practically annihilated, and that out of a party of 12 men of the Derbyshire Regiment which was guarding a drift, 8 men were killed and 4 wounded. Upon Colonel Kekewich being incapacitated by wounds the command of the column was temporarily assumed by Lieutenant Colonel Wylly, Derbyshire Regiment". Official recognition was this time bestowed on exceptional work. Private Bees, one of nine in the maxim detachment, six of whom were hit, went forward to a spruit held by Boers 500 yards away for water for wounded comrades, passing within 100 yards of rocks held by Boers. He brought back a kettle full of water, the kettle being hit several times. Bees was awarded the Victoria Cross. One officer, Lieutenant Mills, who was killed, and 6 non-commissioned officers and men were mentioned in Lord Kitchener's despatch of 8th October 1901 for deeds of magnificent heroism, almost equal to that of Private Bees. Altogether the Derbyshire Regiment had 8 officers and 22 non-commissioned officers and men mentioned in despatches written by Lord Kitchener for surpassingly gallant work, and in his final or supplementary despatch he added the names of 5 officers and 6 non-commissioned officers.

The Mounted Infantry company of the Sherwood Foresters saw a very great deal of fighting and came up to the high standard of the 1st Battalion. Corporal Beet gained the Victoria Cross at Wakkerstroom, in the Orange River Colony, on 27th April 1900. An Imperial Yeoman being wounded in a retirement, Beet remained with him, placed him in cover, bound up his wounds, and by firing prevented the Boers approaching, so that at dark a doctor was able to go to the wounded man's assistance.

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