Canada immediately sent troops to help Britain defend Hong Kong. The deployment was so rapid that the first ship sailed without proper equipment to support the soldiers, most of which was loaded onto a second ship that was sunk before it could get to Hong Kong. The Canadians were ill-equipped to face the invaders and the Japanese overran Hong Kong in three weeks during December 1941, killing or capturing the entire garrison.

Japan was not a signatory to the Geneva Convention and its old guard maintained that to be captured was to be disgraced. Prisoner of War camps were primarily brutal labour camps where prisoners were worked to death. The many who died did so in degradation rather than in battle. Those who survived the beatings, starvation diets and inhuman work conditions were inadvertent heroes who too often lived with the guilt of their own survival.

On 27 Oct 1941, at the request of the British, Canada sent two infantry battalions to bolster the defence of Hong Kong. These troops included 96 officers, 2 nurses and over 1,875 men and NCOs’ of Quebec City’s Royal Rifles of Canada and the Winnipeg Grenadiers.

These troops, ill trained and poorly equipped, had been falsely advised that the Japanese were poor soldiers who disliked night fighting. The Canadians, commanded by Brigadier J.K. Lawson, landed in Hong Kong on 16 Nov 1941, without their vehicles and heavy equipment. Expecting garrison duty only, the Canadians were not prepared for the massive Japanese attack on 8 Dec 1941.

Outnumbered three to one, the British Garrison of 14,500 men, including the Canadians, fought a hopeless battle against a superior, well-trained, well led Japanese force.

On 25 December, the British Garrison was forced to surrender. The Canadians, fighting bravely and valiantly against hopeless odds, lost 290 killed and almost 500 wounded. During the subsequent long, brutal imprisonment by the Japanese, who considered surrender cowardice, another 260 more Canadians died before Japan itself surrendered in 1945.

Often referred to as Canada’s forgotten battle, the defence of Hong Kong was an attempt by the British government to show that it was prepared to fight to retain its Asian interests. In reality, any defence of Hong Kong against a superior Japanese enemy would be a disaster. In fact, when Winston Churchill was approached about the possibility of reinforcing the British with Canadian troops, he said; "This is wrong. If Japan goes to war there is not the slightest chance of holding Hong Kong or relieving it. It is most unwise to increase the loss we shall suffer there. We must avoid frittering away our resources on untenable positions."

Never the less, the British war office requested troops and Canada responded by sending two battalions of garrison trained troops to Hong Kong. The result was one of the greatest, unnecessary losses of Canadian soldiers during the Second World War. Even ordinary soldiers became aware of the futility of any defence of Hong Kong when, during a shipboard briefing, a soldier said; "My God, another Dunkirk." A second soldier answered; "No fella, at Dunkirk they had somewhere to go."

These words would be prophetic. After only five days of fighting, the remaining British, Canadian and Indian soldiers were forced back for a last stand. On 18 Dec, the Royal Rifles launched several bloody counter attacks suffering many casualties.

'D' Company of the Winnipeg Grenadiers stubbornly refused to allow the Japanese access to the north–south road across the Island until 22 Dec. Finally, facing overwhelming enemy forces, 'D' Company, numbering only 38 wounded men, was forced to surrender.

On 23 Dec, the Rifles retreated, fighting to Stanley Fort. The Winnipeg Grenadiers meanwhile, were fighting on the Western side of the Island at Mount Cameron. Brigadier Lawson was killed in hand to hand fighting on 19 Dec and the remaining Canadians were finally forced off Mount Cameron on 23 Dec. A general surrender to the Japanese began on Christmas Day, 25 December 1941. The battle was over.

A few miles East, Winnipeg Grenadier Company Sergeant-Major John Osborn, led a successful counter attack against the Japanese on Mount Butler. During the attack, CSM Osborn had picked up several enemy hand grenades and threw them back at the Japanese.

Finally, desperately, he fell on a grenade saving a sergeant and his section of men from certain death. For his conspicuous and unselfish bravery, CSM John Osborn was posthumously awarded the Victoria Cross, the first awarded to a Canadian in the Second World War.

Another incident involved the mascot of the Royal Rifles, a Newfoundland dog named Gander. The dog ran off with a Japanese hand grenade, which had landed near a section of soldiers. When the grenade exploded, Gander died, but 7 soldiers lived. Sixty years later, Gander received the Dickin Medal for animal heroism.

Almost 290 Canadian soldiers died during the Defence of Hong Kong and over 500 were wounded. Another 260 Canadians died during captivity as POWs. In total, there were over 2,100 British soldiers killed during the battle and over 2,300 wounded. Almost 11,000 British, Canadian and Indian soldiers were captured and spent the remainder of the war as POWs.