It’s said that pride comes before a fall, and the efficiency with which Japanese forces overwhelmed ‘impregnable’ Singapore in February 1942 certainly dealt a crushing blow to British military pride. The island fortress off Malaya’s tip was nicknamed ‘Gibraltar of the East ’ and served as a vital power base from which British tentacles uncoiled into Southeast Asia.

Japanese forces invaded Malaya in December 1941 – a move coordinated with the attack on the US Navy at Pearl Harbor. Numerically superior British and Indian army battalions hurried north, even as a sustained campaign of air raids on Singapore began. But their opponents were battle-hardened veterans and, when the Japanese gained air superiority, disastrous defeat was assured.

The catastrophe began unfolding when – two days after the invasion – the British capital ships HMS Prince of Wales and HMS Repulse were sunk by torpedo bombers while attempting to shell Japanese landing sites. Light tanks and bicycle infantry allowed invading troops to make a swift advance, arriving at the gates of Singapore on January 31 1942. British sappers blew up the causeway linking Singapore to the mainland, but merely postponed the inevitable.

An intense air and artillery bombardment began and on February 8 a Japanese assault hit Sarimbun beach in the northwest. Once the last of Singapore’s Hawker Hurricane fighter aircraft were neutralized, further tank landings soon outflanked defenders who were driven back into a small pocket in the southeast. Despite Winston Churchill’s rousing ‘fight to the last man’ instruction, surrender seemed the only option. On January 15 the Japanese Rising Sun flag was hoisted atop the Cathay Building, Singapore’s tallest, and what Churchill bitterly called ‘the largest capitulation in British history’ was complete. His anger was righteous. The Japanese commander later admitted that he would have lost the battle had the British fought on.

When: February 15 1942

Where: Singapore

Death toll: During the Malayan campaign Allied forces suffered 50,000 casualties (with 130,000 taken prisoner). The Japanese lost 9,600 men.

You should know: The supremely complacent British attitude before the crushing defeat at Singapore could be judged by gung-ho talk among young army officers who repeatedly expressed disappointment that potential attackers would be frightened off by Singapore’s impressive defenses, thereby denying the Brits a sure-fire opportunity to inflict a huge defeat on ‘inferior’ Japanese forces.

World War II had been taking its grim course for two years without the involvement of the world’s richest and most powerful nation, the United States of America. All that changed on the morning of December 7 1941 when Japanese aircraft launched a surprise attack on the US naval base at Pearl Harbor, Hawaii. The attack was as devastating as it was unexpected; in two separate strikes over 350 Japanese fighters and bombers unleashed their deadly cargo on the pride of America’s Pacific fleet, sinking five battleships and damaging 15 others. During the two-hour attack 188 US aircraft were destroyed; Japan lost just 29 planes. Never imagining such a brazen act of aggression, the Americans had moored their ships in lines, making them even easier targets for the bombers.

Although the standard American portrayal of Pearl Harbor is that of an unprovoked attack that came quite literally out of the blue, Japanese resentment over US economic power in the Pacific and its own dependence on imported natural resources had been festering for some time. In pursuing its expansionist policies in Southeast Asia, Japan may have achieved its short-term objective of disabling the US fleet and thus buying vital time to conquer prized targets in the region such as the Philippines, Malaya and Burma; but the assault on Pearl Harbor failed spectacularly in the long term, for, far from forcing the USA to abandon its presence in the Pacific or indeed to sue for peace, it served to galvanize the previously reluctant nation.

The very next day President Roosevelt declared war on Japan, prompting Germany in its turn to declare war on the USA, achieving finally what Churchill had been praying for since 1939: America’s entry into the European conflict on Britain’s side.

When: December 7 1941

Where: Pearl Harbor, Oahu, Hawaiian Islands (USA)

Death toll: 2,402 Americans were killed in the attack, including 1,177 on the USS Arizona alone when it was blown up and sunk. Japanese losses were 64.

You should know: There has been much debate over the failure of US intelligence to gain advance warning of the Japanese plan, it seems particularly strange that no one detected a 30-strong fleet which spent 11 days travelling 6,500 km (4,000 mi) across the Pacific.

If there was one thing at which Germany’s well-trained and disciplined Wehrmacht excelled, it was Blitzkrieg (lightning war). This was modern warfare at its most shock-and-awesome, involving air supremacy and the rapid advance of powerful tank columns supported by mechanized infantry. And it was Blitzkrieg that Hitler relied on when he ripped up his pact with Stalin. It had suited the two dictators to carve up Eastern Europe between them in 1939, but uneasy peace between two diametrically opposed ideologies was never going to last.

German forces invaded Soviet territory in June 1941 in a pre-emptive strike codenamed Operation Barbarossa. The prolonged conflict that followed would become the largest military offensive and most lethal battle in world history. Despite occupying huge swathes of the Soviet Union, including key economic areas like oil-producing Ukraine, Operation Barbarossa would prove disastrous. German troops got to within just 16 km (10 mi) of Moscow in December 1941 before revitalized defenders – aided by the onset of harsh winter – held them off in the desperate Battle of Moscow. It was the turning point.

As with Napoleon before him, Hitler’s ambition to slay the Russian Bear had been thwarted by the iron hand of winter. From the Christmas of 1941, the Wehrmacht would be driven back inexorably in a long and bloody fight that included terrible episodes like failure of the prolonged siege of Leningrad and catastrophic defeat in the battle of Stalingrad. Along the way, millions of lives would be lost on both sides. The final drama was eventually played out when rampaging Russian troops entered Berlin in April 1945. If the self-delusional Adolf Hitler still refused to accept that his decision to mount Operation Barbarossa had led directly to Germany’s defeat in World War II, he must surely have known it then.

When: From June 22 1941

Where: Western Soviet Union

Death toll: Uncountable. War on the Eastern Front is estimated to have cost Soviet forces 7,000,000 casualties, while Axis powers lost 4,200,000 troops. Civilian deaths are thought to have reached 20,000,000.

You should know: Stalin can have been under no illusion about Adolf Hitler’s intentions. Hitler’s views on the Soviet Union were made clear in Mein Kampf (My Struggle), published in 1925, wherein the future Fuhrer promised to invade vast lands to the east to provide the Aryan German master race with Lebensraum (living space), simultaneously subjugating ‘lesser’ Slav peoples.

The so-called phony war ended in May 1940 when the Battle of France began. It would end in disastrous defeat for the Allies. In phase one of the battle, Fall Gelb (Operation Yellow), the Wehrmacht’s rapid advance outwitted Allied Forces defending Belgium in anticipation of Germany repeating its World War I attack plan. This time Germans poured through the Ardennes Forest (a feat thought impossible by Allied strategists) and outflanked the defenses.

After fierce fighting, the British Expeditionary Force (BEF) – along with many French soldiers – was driven back to the sea and mounted a defiant last stand. This – and Hitler’s decision to hold back his generals for three days and leave the task of preventing the BEF’s escape to the Luftwaffe – allowed Britain to organize Operation Dynamo. The dramatic evacuation of 338,000 mainly British troops from the beaches of Dunkirk by the Royal Navy and the famously gallant flotilla of small boats took place between May 27 and June 4.

Having mopped up resistance in the northwest, the Germans began phase two of the battle on June 5. Fall Rot (Operation Red) involved outflanking France’s vaunted (but ultimately useless) defensive Maginot Line, smashing through demoralized defenders and heading through the French heartland towards Paris. The government fled to Bordeaux and Paris fell on June 14. Newly elected French leader Marshal Petain sued for peace and an armistice was signed on June 25. The Battle of France was over, barely six weeks after it began.

If there was a glint of silver in the Allies’ dark cloud, it was Dunkirk, where the soundly trounced BEF turned the tables by slipping away before the Wehrmacht’s steel jaws snapped shut, living to fight another day… a great escape that probably prevented Germany from winning World War II in 1940.

When: May 10 to June 25 1940

Where: Northern France

Death toll: Approximate casualty figures in the Battle of France were 170,000 Allied and 49,000 German dead.

You should know: Hitler later suggested that he allowed the BEF to escape from Dunkirk as a gesture of goodwill, in the hope that Britain would appreciate his merciful gesture and be encouraged to enter into a negotiated peace settlement. But the facts don’t support this claim – the German army’s Directive 13 issued on May 24 called for the total annihilation of all forces within the Dunkirk pocket.

The Royal Navy’s HMS Royal Oak was a Revenge-class battleship that saw action in World War I. But by 1939 Royal Oak was too cumbersome to engage in the new sort of flexible naval warfare that would no longer involve mighty battleships pounding each other in set-piece battles. Six weeks into World War II she lay in Scapa Flow, Britain’s great naval base in the Orkneys. It wasn’t a safe harbor. German submarine commander Karl Donitz was planning a daring raid that would exact revenge for the humiliating scuttling of the German fleet in Scapa Flow in 1918, and also weaken Britain’s ability to protect Atlantic convoys.

His chosen weapon was U-47, commanded by Gunther Prien. On the moonless night of October 13 the submarine brazenly entered Scapa Flow on the surface, only to find the anchorage almost empty. Prudently, much of the fleet had been dispersed, though Royal Oak and a few others remained. At 00.58 U-47 fired a salvo of torpedoes at the unsuspecting battleship. One struck her bow six minutes later, causing the startled crew to think there had been an on-board explosion. Prien fired again, using his stem tube, and missed. But a second salvo from the bow tubes struck home, wreaking havoc. A fireball engulfed Royal Oak’s interior and she rolled onto her side before sinking at 01.29, just 13 minutes after the second attack.

Over 800 crew members perished on the stricken ship and in Scapa Flow’s icy waters.

The loss of Royal Oak had a seriously negative effect on morale, but at least the ease with which U-47 slipped in and out of Britain’s main naval base and sank a capital ship ensured that home sea defenses were immediately tightened, making any repeat of the disaster much less likely.

When: October 14 1939

Where: Scapa Flow, Orkney Islands, Scotland, UK

Death toll: 833 from the ship’s complement of 1,234 perished

You should know: Today, Royal Oak’s upturned hull lies just 5 m (16 ft) below the surface of Scapa Flow. The wreck is a designated war grave that may not be visited by divers, save those from the Royal Navy who go down each year on the anniversary of the sinking to place a White Ensign at her stem.

Can there ever have been a greater military disaster than the Battle of the Somme? It seems unlikely. One side’s disaster is often the other side’s triumph, but this fearful encounter on the Western Front was a catastrophe for Allied and German troops alike. It was World War I’s most infamous battle – a prolonged engagement lasting for nearly five months that claimed over 1,100,000 lives with over 60,000 falling on the first day, July 1 1916.

The battle ostensibly took place to relieve German pressure on Verdun, where French defenders had been taking heavy casualties. But in reality both British and French governments were under intense pressure to deliver military achievements. Despite serious reservations expressed by the head of the French army, General Foch – backed by senior British commanders – political pressure ensured that the view of Britain’s commander-in-chief prevailed. Field Marshal Douglas Haig believed grinding attrition – whatever the cost – was the way to weaken and beat the Germans.

He also wrongly believed that artillery would destroy enemy defenses. Over 1,700,000 shells were fired on the eve of battle, but the Germans retreated to deep dugouts and popped up when the barrage stopped, ready and able to repel the Allied advance. This came on a 40 km (25 mi) front and marked the start of a bloody stalemate. When the Battle of the Somme finally ended in November, the Allies were able to claim Pyrrhic victory. They had gained a strip of ground 48 km (30mi) wide and 11 km (7 mi) across at its deepest point.

If ever a single event epitomized the tragic futility of the trench warfare for which the Western Front became notorious, it was the Battle of the Somme. This one inconclusive encounter made a major contribution to the war’s overall casualty figure of 15,000,000 dead.

When: July to November 1916

Where: On both banks of the River Somme, Northern France

Death toll: Around 1,120,000 casualties were recorded during the battle (500,000 German, 420,000 British and 200,000 French), in addition, countless combatants were seriously wounded.

You should know: As an indication of how outmoded British military thinking was in 1916, a key element of the General Staff’s plan for the Battle of the Somme involved unleashing a regiment of cavalry to charge through the hole that was supposed to be punched in the German lines by advancing infantry, it never happened. The tactic had worked well in the English Civil war over 250 years before but was ludicrously inappropriate for 20th-century trench warfare.