The Battle of Singapore and the Japanese Occupation (1942–1945)

On 7 December 1941, Japan attakked Pearl Harbor and the Pacific War began in earnest. One of Japan's objectives was to capture Southeast Asia and secure the rich supply of natural resources to feed its military and industry needs. Singapore, the main Allied base in the region, was an obvious military target. The British military commanders in Singapore had believed that the Japanese attack would come by sea from the south, since the dense Malayan jungle in the north would serve as a natural barrier against invasion. Although the British had drawn up a plan for dealing with an attack on northern Malaya, preparations were never completed. The military was confident that "Fortress Singapore" would withstand any Japanese attack and this confidence was further reinforced by the arrival of Force Z, a squadron of British warships dispatched to the defense of Singapore, including the battleship HMS Prince of Wales, and cruiser HMS Repulse. The squadron was to have been accompanied by a third capital ship, the aircraft carrier HMS Indomitable, but it ran aground en route, leaving the squadron without air cover.
On 8 December 1941, Japanese forces landed at Kota Bahru in northern Malaya. Just two days after the start of the invasion of Malaya, Prince of Wales and Repulse were sunk 50 miles off the coast of Kuantan in Pahang, by a force of Japanese bombers and torpedo bomber aircraft, in the worst British naval defeat of World War II. Allied air support did not arrive in time to protect the two capital ships. After this incident, Singapore and Malaya suffered daily air raids, including those targeting civilian structures such as hospitals or shophouses with casualties ranging from the tens to the hundreds each time.
The Japanese army advanced swiftly southward through the Malay Peninsula, crushing or bypassing Allied resistance. The Allied forces did not have tanks, which they considered as unsuitable in the tropical rainforest, and their infantry proved powerless against the Japanese light tanks. As their resistance failed against the Japanese advance, the Allied forces were forced to retreat southwards towards Singapore. By 31 January 1942, a mere 55 days after the start of the invasion, the Japanese had conquered the entire Malay peninsula and were poised to attack Singapore.

Lieutenant-General Arthur Percival, led by a Japanese officer, marches under a flag of truce to negotiate the capitulation of Allied forces in Singapore, on 15 February 1942. It was the largest surrender of British-led forces in history.
The causeway linking Johore and Singapore was blown up by the Allied forces in an effort to stop the Japanese army. However, the Japanese managed to cross the Straits of Johor in inflatable boats days after. Several heroic fights by the Allied forces and volunteers of Singapore's population against the advancing Japanese, such as the Battle of Pasir Panjang, took place during this period. However, with most of the defences shattered and supplies exhausted, Lieutenant-General Arthur Percival surrendered the Allied forces in Singapore to General Tomoyuki Yamashita of the Imperial Japanese Army on Chinese New Year, 15 February 1942. About 130,000 Indian, Australian and British troops became prisoners of war, many of whom would later be transported to Burma, Japan, Korea, or Manchuria for use as slave labour via prisoner transports known as "hell ships." The fall of Singapore was the largest surrender of British-led forces in history.

Singapore, renamed Syonan-to (昭南島 Shōnan-tō, "Light of the South Island" in Japanese), was occupied by the Japanese from 1942 to 1945. The Japanese Occupation is the darkest period of Singaporean history as the Japanese army imposed harsh measures against the local population. Numerous atrocities were committed by Japanese troops, particularly by the Kempeitai, the Japanese military police. They were the enforcers of the Sook Ching Massacre of Chinese civilians, to retaliate against them for their support of the war effort in China. The mass executions claimed between 25,000 and 50,000 lives in Malaya and Singapore. The rest of the population suffered severe hardship throughout the three and a half years of Japanese occupation.