After a brief attempt to defend a line closer to the Transvaal, at Dundee, Lieutenant-general Sir George White, the British commander in Natal, had withdrawn to Ladysmith. The British army in Natal had concentrated in Ladysmith by the early morning of 25 October. The Boers, under Commandant-General Joubert were approaching, ready to embark on a siege of the town.
White decided to launch a pre-emptive strike on the approaching Boers before they could establish their lines. One force was sent north to guard Nicholson’s Nek. The main attack was to be launched first against Long Hill, north east of the town, and then turn left to attack Pepworth Hill, north of the town. White assumed that the left wing of the Boer line was on Long Hill. He was wrong. The Boers were not on Long Hill. They were on Lombard’s Kop, to the east of the town. The British force would be advancing into a gap between two Boer positions.
Command of the attack on Long Hill was given to Colonel Geoffrey Grimwood, a veteran of much combat in India. He was given the 8th Brigade (1st King's Royal Rifles, Royal Dublin Fusiliers, 1st King's Liverpool and 1st Leicestershires) to capture the hill. The 7th Brigade (1st Devonshire, 1st Manchester, 2nd Gordon Highlanders, 5th Dragoon Guards, 18th Hussars and the Imperial Light Horse) under Colonel Ian Hamilton was to act as a reserve until Long Hill was secure, then move directly against Pepworth Hill. The artillery was to advance between the two brigades. Finally Major-general Sir John French's Cavalry Brigade (5th Lancers, 19th Hussars and Natal Carbineers) was to guard the right flank of the advance. All of this was to be achieved after a night march.
Just about everything that could go wrong did. During the night march the artillery received new orders, and turned off to the right. Two of Grimworth’s battalions followed them. At dawn he found himself at the bottom of an empty hill, with half of his force missing. French had also got lost in the night, and was not in place to cover Grimworth’s right flank.
Grimworth’s men now came under fire from the Boers on Pepworth Hill and Lombard’s Kop, and from yet more Boers to the east. Grimworth seems to have panicked under fire, and lost control of the situation. Hamilton’s attack had to be diverted from Pepworth Hill to support Grimworth. French had finally caught up, and now made up the southern (right) flank of the British line. However, even the combined British force found it could make little progress against the Boer riflefire.
To make things worse, the Boer’s 155mm Creusot gun on Pepworth Hill, known to the British as Long Tom, now opened fire on Ladysmith. Rumours began to reach the town of another Boer force approaching from the north. If true, then the tiny garrison that had been left in the town would have had very little chance of keeping it out for long enough for the main force to get back. Perhaps fortunately, the Boers north of Ladysmith were concentrating on the destruction of Carleton’s force, which was under attack on a hilltop to the north (Battle of Nicholson’s Nek). The commander of the garrison sent an urgent request for help to General White.
He was already aware that his plan was not working. At just after noon he ordered a retreat. This led to one of the great missed chances of the Boer War. The British withdrawal threatened to descend into chaos. Only the artillery remained in place to cover Grimworth’s retreat. The Boer horsemen could have caused chaos, and Joubert’s officers begged him to let them attack. However, Joubert was one of many Boers who felt that it was un-Christian to attack a fleeing foe. The British pursuit of fleeing Boers at Elandslaagte had caused much anger amongst the Boers. Joubert stuck to his beliefs, replying with a Dutch saying – “When God holds out a finger, don't take the whole hand”. The British were allowed to retreat back into Ladysmith.
Just as the battle was drawing to an end, the navy made a dramatic appearance on the scene in the shape of a party of 280 sailors with six large guns. These finally gave White the range to return the fire of the Long Tom on Pepworth Hill, which soon broke off firing, at least for the day. The naval guns were not enough to turn the tide of the day, but they did cheer the inhabitants of Ladysmith.
That cheer was badly needed. Later in the day news arrived of the surrender of Carleton and his men on Tchrengula Hill. The two battles, at Nicholson’s Nek and Lombard’s Kop, came to be known as “mournful Monday”. The gloomy mood in Britain was only lightened by the knowledge that a powerful expeditionary force was on its way to South Africa. The very next day General Sir Redvers Bullers, the commander of that force, arrived at Capetown.
Joubert now settled down to conduct a regular siege. This was a major mistake. The Boers temporarily had a numerical advantage. They were much more mobile than the British. If Joubert had continued with his push towards Durban and the sea he could have made much more effective use of his men. By allowing his men to get bogged down in a siege Joubert effectively handed the initiative in Natal back to the British. Over the next four months the story in Natal stops being one of Boer advances and becomes one of British attempts to raise the siege of Ladysmith.