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Retreat from Kabul, 1842
During the ‘Great Game‘ Britain greatly feared that the Russian Empire’s expansionism could spill into the Asian subcontinent. To counter this threat, they moved to establish a presence in Afghanistan (a buffer between the two empires) and install a pro-British regime. In 1839 a 20,000 strong army with 40,000 civilians in tow removed Dost Mohammad and replaced him with the pro-British Shuja Shah. For a time around Kabul all was peaceful, and so, many of the occupying regiments were returned south. Yet, a seething contempt for these infidels had been sown amidst the tribes of the hill-lands around.
In November 1841 open revolt broke out around Kabul. The British now realised how isolated and vulnerable they were. Their army’s strength was just 4,500 strong but 14,000 civilians still remained. Under Major General Elphinstone‘s limp leadership, British authority and security quickly deteriorated and the only course of action remaining was to negotiate a peaceful withdrawal. But they would be betrayed successively, despite repeated assurances. As they began their march towards Jalalabad, the largely defenceless mass of British-Indians was harried at every opportunity. Once they entered the Khyber Pass their fate was sealed. There, Afghan tribesmen ambushed and massacred them en-mass as the troops, including a battalion of redcoats, tried to fight a way through. Just one Briton made it back across the North-West Frontier. Most of 16,500 would never be seen again.
The annihilation left Britain and India in shock. Governor General Lord Auckland suffered an apparent stroke upon hearing the news. The reputation of the British East Indian Company was now cracked; “Men remembered Kabul” commented a British officer at the outbreak of the great Indian mutiny 15 years later.
Indian Rebellion, 1857
When a third of the entire Indian sepoy army mutinied it was because, infamously, the paper cartridges for their rifles were greased with pig and cow fat, the handling of which was intolerable to sepoys Muslim, Hindu, both. Of course, the true roots to this great uprising went much deeper. When security in Britain’s ‘jewel in the crown’ collapsed in May of ’57 it incited panic throughout the halls of Westminster.
It was a days’ ride north of New Delhi where sepoys of the 3rd Cavalry Regiment first turned on the British officers and their families in a frenzied spree of slaughter. From that spark, the mutiny spread like wildfire. The rebels moved to occupy Delhi in their tens of thousands and proclaim Bahadur Shah Zafar ruler of their rebel state, regardless of his wishes. Meanwhile, vast swathes of Crown territory in central India were suddenly no-go zones for the thousands of British soldiers and civilians. They fled, they hid, and were hacked down with little mercy when caught. Isolated units of British, cut off, held out desperately against bloodthirsty mutineers as the walls of their once orderly world collapsed around them. British High Command rushed redcoats away from other theatres of operation to reinforce British-Indian forces as they struggled to regain the initiative. The prospect of laying siege to the massive walls of New Delhi lay ahead with it’s vast rabble of rebels.
A year later and the mutiny was stamped out but thousands of British including many women and children had been butchered, the stories of which dismayed the public back home. Many, many more Indians were also slaughtered in revenge, however, most of them victims too.
Battle of Ridgeway 1866
Like at Saint Denis, another embarrassing episode for Crown forces in Canada that wasn’t exactly the worst military setback to ever occur. Out of all the many adversaries the British confronted over the centuries, they faced an odd one near the Niagara Falls one June. The Irish-American Fenian Brotherhood had launched a campaign of raids into the Canadian Provinces with the aim of inducing enough of a strategic crisis in Westminster for them to withdraw crown forces from Ireland. Most raids came to naught. At Ridgeway, however, 900 British-Canadian redcoats were defeated in battle against a smaller army of Irish-American irregulars.
It appeared to be the professionals vs a rag-tag band of amateurs, but not so; the invaders were actually recently demobilised Civil War veterans whilst the Canadian soldiers were greenhorns. The Fenians managed to ferry many hundreds of men across the Niagara in the dawning hours of June before US Navy riverboats could intercept them. Once in Canada, they moved to secure Fort Erie before marching to face colonial forces at Ridgeway. There, battle was joined and the Canadians initially fought off Fenian skirmishers and appeared to be winning. But something went wrong. It’s not clear what happened but it appears Fenian mounted scouts were mistaken for charging cavalry. The Canadians tried to form a square formation to defend against it but in the disarray this caused, the Fenian commander seized his opportunity and ordered a bayonet charge. It completely routed them and the Fenians stood victorious. Another smaller Canadian force was then defeated. However further operations against provincial forces massing to confront them seemed futile so they slipped back across the border.
This embarrassing trouncing would shame the colonial administration into forging a more effective force with which to defend Canada that would become the Canadian Army.
Battle of Isandlwana, 1879

The British suffered a severe loss of face when a seasoned battlegroup was annihilated by an impi of spear-wielding Zulus in modern-day South Africa. By the late ’70s, the British implemented a scheme to consolidate their grip over Southern Africa but the independent Zulu and Boer Republics stood in the way. The inevitable solution was to feign grievances they could use to justify subjugating them through war. Zululand was first in the crosshairs and General Lord Chelmsford marched an army across the border at the years’ start. But King Cetshwayo reacted boldly and sent a force of 20,000 warriors to repulse him.
Chelmsford set up camp at Isandlwana. Aware that an enemy force was in the field, the hubristic general set out with the bulk of his army to find it. He was sure that the remaining force of 1,800 infantry, artillery, and various other units, including 700 British, had the firepower to fight off any Zulus alone. Yet the Zulus possessed a great warrior culture. They were mobile and highly-disciplined in battle. Nimbly manoeuvring across the landscape, the large Zulu impi edged past Chelmsford’s force to arrive five miles from Isandlwana before it was detected. Once the cat was out the bag, they rushed towards the encampment. Minutes after scouts back in camp raised the alarm sentries abruptly spotted hordes of blacks swarming towards them in densely packed ranks. The infantry rushed to deploy in the ‘thin-red-line’ formation and deliver volley fire into the onrushing Zulus. For a while, they kept their enemy at bay. Their linear formation provided little defence for their flanks, however, and as the infantry began to tire the Zulus could be held off no longer. Dismayed, it became apparent the camp was being overrun. Thousands of warriors, running and shouting and stabbing, swarmed around beleaguered pockets of redcoats who stood forlornly before they fell.
A stunned Lord Chelmsford returned to the camp to discover the corpses of 1,300 slain, including 52 officers – more killed than at the Battle of Waterloo. Ultimately, the British Empire would win their war against the Zulus, but the martial prowess performed at Isandlwana ensured their continued independence from British imperialism, for a while at least.
Battle of Majuba Hill, 1881
The Boers would be a persistent thorn in the side during the late 19th Century. The British made the fatal error of assuming that an enemy army manned by rustic farmers was a third rate army, by default. The Boer burghers, however, were excellent hunters and this meant that whilst they eschewed close combat they brought to the battlefield the kind of small arms handling more familiar to a ‘Tommy’ than a ‘Redcoat’. It took two bloody wars before the British subdued the Boers with a revamped military doctrine appropriate for the 19th Century’s dusk.
In the 1st Boer War, the British had been struggling to cow the Boers in battle for peace to be negotiated on their terms. After only a couple of months, though, it seemed the Boers could soon be brought around the negotiating table and this expensive conflict be brought to an end. Major General Sir Colley felt this was time to emphasise the strength of Briton’s position by occupying Majuba Hill. This summit rose 1100ft (335m) over a surrounding area of Boer defences and the General believed the Boers would abandon their defences as untenable. The General was wrong.
When 400 infantry appeared atop Majuba, the immediacy of the threat triggered Boer commanders Smit and Ferreira to fight, not flight. They quickly formed bodies of riflemen to dart up a hill that was actually considered by many unscalable for military purposes, and therefore Colley hadn’t bothered to dig in to defend. The Dutch commandos, swarming up the mountain using groundbreaking fire-and-movement tactics, decimated the British ranks with relentless sniping. Whilst the British soldiers were exposed and blind, their tormentors were hidden and well-aimed. The British were fighting a downhill-battle like it was them down the hill. Morale then tumbled downhill and men began to break lines to chase it thus. As the Dutch threatened their flank, the rest of the British turned tail. General Colley paid for his inert leadership with his life. The British force of professionals was swept off the battlefield by a force of farming men and boys. A month later, the war was lost and Boers won their freedom from the grip of the Empire’s tendrils… for now.
‘Black Week’, 1899
‘Black Week’ occurred soon after the start of the 2nd Boer War when the British suffered an unheard-of three successive major defeats. The Boers kicked off the war when its commandos marauded into British South Africa, cutting railway lines and laying siege to three cities. Naturally, the British counteracted and moved north in three prongs to relieve said cities, yet between the 10th-15th of December, traditional British army tactics failed in the teeth of the Boers’ excellent rifle fire and high mobility.
On the 10th, an all-arms force of 2,000 moved to retake a major railway junction at Stormberg and after an exhausting all night march where they got lost, they made a hasty assault the moment the enemy were sighted on a kopje. The assault immediately floundered, and before anyone could get any kind of bearings the troops retreated. They were chased back to their starting point by mounted Boers whilst the force’s flustered commander failed to realise he had left 700 infantry behind to be captured.
The next day a much larger force of 15,000 British assaulted 8,500 Boers at Magersfontein. The Boer positions were poorly recced and so the artillery bombarded the slopes above the Boer positions merely alerting them to the impending assault. The British soldiers, headed by a highland brigade, advancing in pitch blackness and torrential rain, their ranks packed tightly, stumbled into rifle-fire range of the Boer positions. They opened withering fire and, within minutes, 700 men, including Major General Wauchope fell. The Highlanders were pinned down. Despite efforts to regain the initiative, by the afternoon the Brits were forced to fall back to lick their wounds.
And at Colenso, 15,000 redcoats blundered into Boer positions on the Tugela River on the 15th. One brigade with General Hart at the lead was misdirected and got jammed on the loop of the river where the Boers gleefully raked them with fire. Two batteries of artillery also advanced, unaware of the fact they were marching right into the burghers’ crosshairs. The Dutch couldn’t resist and fire erupted from a thousand-odd rifles. Scores of gunners were picked off in minutes. Dazed and battered, the army withdraw leaving behind almost a thousand dead and wounded, and more to be taken prisoner.
Battle of Spion Kop, 1900
The British, reinforced after the trauma of ‘Black Week’, were still labouring to relieve Ladysmith after almost three months of siege. General Buller decided on seizing Spion Kop because the hill stood slap-bang in the centre of Boer positions around Ladysmith. 20,000 troops, Mahatma Gandhi and Winston Churchill included, and General Woodgate in direct command, moved to seize the summit on January the 23rd.
Making the ascent in dense mist and pitch black are never the best conditions to navigate in, so when 1,700 infantry captured the lightly held hill-crest, by dawn it turned out to be a lower plateau overlooked by three crests of the true summit. And they were occupied by the enemy. Woodgate had come prepared to entrench but hill-rock restricted such efforts. British positions came under pitiless shelling and sniping. The Boer command knew their hold over the summit was still vulnerable so ordered 300 commandos into a rare frontal assault. The fighting raged, vicious, close-quarter; the British, lunging with fixed bayonets, Boers, slashing with knives, their rifles cracking bones. They reached the crestline before they could be checked. A stalemate now developed around the Kop and casualties continued to mount. General Woodgate and a couple of his staff officers then fell leaving the British soldiers pinned down, confused, and now leaderless. Their artillery didn’t help either with one soldier writing later: “our gunners, by the inaccuracy of their fire did far more damage to our front line of infantry than to the Boers!” Hard fighting continued and their positions were held with the aid of reinforcements. Although some of the men were cracking under the strain, more fresh troops seized the summit. Victory for the Brits seemed to be within their grasp because the following morning, the shattered Boers actually withdrew from Spion. The surviving British commander was ignorant of this, however, and believed Spion could not be held, so he, too, withdrew his men and the Boers quickly returned.
The British suffered 1,500 casualties in yet another defeat. The tables soon turned for the Brits as their massive war machine went through the gears to ground the Boer Republics into submission. Alas, the Boers ‘won the battles, but lost the war.’ The British Empire’s veneer of impenetrability was now gone, however.
First Day of the Battle of the Somme, 1916

World War I lives in our memory for the callous, almost industrial-like efficiency countless soldiers’ lives were snuffed out on the meat-grinder battlefields of northern France. And of all the times the British hammered in vain at the German shield, at the Somme many thousands of men were lost in an instant. This battle followed the format of most on the Western Front but on an obscenely large scale. For over four months 2.5 million Allied soldiers, over half of whom were drawn from the British Commonwealth, attempted to give the Germans a bloody nose in 12 sub-offensives, each a major battle in its own right.
Massed assaults of infantry were preceded by epic artillery bombardments that rarely had the debilitating effect on German trenches British Army HQ planned for. Once over the top, the infantry had to face scything machine gun fire before they could reach German trenches. The nadir was reached on the first day of the battle. Masses of Fourth Army ‘Tommies’, shredded by bullets and blown to pieces by artillery shells across a hellscape of destruction and din, suffered 57,000 casualties including 19,000 dead. It is the highest death toll ever suffered by the British Army in one day.
Kilmichael Ambush, 1920
The Irish War of Independence was a low-level guerrilla war with little conventional fighting as the Irish Republican Army (IRA) lacked the arms and ammo. IRA ‘flying columns’ were adept at ambushing isolated security forces, however. The British deployed a paramilitary force to support the police and these consisted of WW1 army veterans who quickly became notorious for their violence and ill-discipline towards the Irish populace. Subsequently, these ‘black and tan’ units were prioritised for ambushes and the most deadly of these occurred in County Cork in late November.
Three dozen IRA soldiers carefully prepared an ambush for 18 ‘black-and-tans’ travelling in two lorries. It was triggered when the IRA commander managed to flag down the first lorry then hurled a bomb at the cabin, signalling the surrounding IRA to open fire. A savage, close-quarter fight erupted. The black and tans were sitting ducks and were gunned down to a man, just one survivor was left for dead. For the British Government, although the numbers lost were negligible it alarmed them how easily these elite troops were wiped out. For the Irish, it was a morale boosting victory that ensured their fight for independence would grow and ultimately succeed.
Sinking of HMS Royal Oak, 1939
Whilst plenty of large warships have sunk in the Royal Navy’s history, taking down hundreds of sailors each time, the sinking of HMS Royal Oak stands out because it jarred the British out of a period of calm and into the carnage of total war. HMS Royal Oak was a 30,000-ton Revenge-class battleship armed with 15-inch (381 mm) guns and 1,200 crew. By 1939, as the war was still in its ‘Phony’ stage, the battleship was showing her age. She was relegated to defending the Scapa Flow naval bastion with her decent anti-aircraft armament.
The German Kriegsmarine, however, was scheming to send a submarine to attack Scapa Flow. An Aladdin’s cave of targets was just waiting to be torpedoed there. In what Sir Winston Churchill described as “a remarkable exploit of professional skill and daring”, submarine U-47 managed to sliver past blockships and islands obstructing entry into Scapa anchorage to sink the Royal Oak with four torpedoes. She sank in 13 minutes taking down 834 souls, including Rear-Admiral Henry Blagrove. 134 boy-seamen, the youngest just 15, also had their blossoming lives extinguished – the most in any one ship loss.
The result of this surprise raid on Britain’s premier naval base meant it had to be virtually abandoned whilst Admiralty upgraded its defences. It struck an ominous tone for what was to come.
Fall of Singapore, 1942

At a time when Britain was suffering disasters left, right and centre, the Fall of Singapore was the worst military disaster to ever befall the British, traumatising Prime Minister Winston Churchill for years after, such were its consequences to British global standing.
Singapore was supposed to be a bastion of sea power that could host a formidable fleet and was guarded by massive naval artillery pieces, plus a large garrison. Yet Britain’s illusion of strength in the Far East began to unravel just a day after Japan’s entry into WW2. Japan invaded Malaya, and because the British had overestimated how impassable the Malayan jungle was and were anyhow under-resourced, the Japs managed to capture the entire peninsula in just seven weeks. Now, all that stood between the Japanese and ‘Fortress Singapore’ was a strait 10 miles wide.
The aforementioned garrison numbered 85,000 Commonwealth troops (including a full division of British) plus hundreds of heavy guns. Failures of command-and-control meant that a soft spot in the north-western coast defences was identified and exploited for the Japanese force, outnumbered 2-to-1 by Commonwealth troops, to secure a beach-head. Despite some resolute defending, particularly by Australian battalions, central command failed to gain the tactical initiative and defending forces were pushed inland into urban areas. A week beyond the initial landings and British supplies were running low; the island’s water supply was being bombed and was failing, spelling doom for any hopes they could hold out. 5,000 fell in the defence of Singapore and the remaining 80,000 were taken prisoner. A total 130,000 Commonwealth troops in Malaya and Singapore, including 40,000 British, trudged into captivity after just nine catastrophic weeks of defence.
Battle of Imjin River, 1951
Four years after what is regarded as the moment the British Empire ended – the partition of British India – a battalion of British infantry was effectively destroyed during the Korean War. By 1951, the military initiative had been seesawing between the two adversaries as the American led UN struggled to blunt the human wave assaults of the Chinese ‘Red Wave’. In late April, the Communists went on the offensive again and attacked the British 29th Brigade, thinly stretched out over 12 miles (19km).
Over the next few days, the brigade was forced back from a defence line on the Imjin. Despite tenaciously defending their positions, the Chinese were simply too many and swamped any allied unit that couldn’t conduct a fighting withdrawal quickly enough. One of the brigade’s four constituent battalions, 1st Battalion the Gloucester Regiment, was one of those units. Its soldiers paid the price for their stubborn defence of the Imjin River by getting cut off. They withdrew to Hill 235 to make a final stand and hope forlornly for rescue. A number of allied counter attacks were made to try to effect this, yet failed after two days of fighting. The Glosters were exhausted and many were wounded. Their commander, Colonel Carne, surrendered. Himself and 459 soldiers were marched into Chinese captivity.
The battalion was destroyed whilst 29th Brigade was forced to beat a hasty retreat. 1st Battalion’s sacrifice is generally regarded to have prevented the Communists from capturing Seoul later.
Dishonourable Mentions
Battle of Prestonpans, 1745 – A small British army was on the wrong end of a Highland Charge when it was attacked by a Jacobite army near Edinburgh. The Redcoats were swept from the battlefield in 30 minutes with about half fallen or captured. For a couple of months at least, Westminster had the spectre of a hostile army on mainland Britain to contend with.
Battle of France, 1940 – An episode most harrowing for British strategic command; when the mass of Allied armies defending northern France, including 13 divisions of the British Army, were absolutely overwhelmed by the German Wehrmacht, wielding its revolutionary blitzkrieg tactics. The Brits suffered 60,000 fallen and captured and lost hundreds of thousands of tons of equipment in their dash to evacuate from Dunkirk.
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