Battle of Pasir Panjang The Battle of Pasir Panjang , which took place between 13 and 14 February 1942 , was part of the final stage of the Empire of Japan ' s invasion of Singapore during World War II . The battle was initiated upon the advancement of elite Imperial Japanese Army forces towards Pasir Panjang at Pasir Panjang Ridge on 13 February . 13 , 000 Japanese troops had made an amphibious landing in the northwest part of Singapore near Sarimbun ( see Battle of Sarimbun Beach ) , and had started to advance south towards Pasir Panjang . They had already captured Tengah Airfield en route . The 13 , 000 soldiers constituted a significant part of the total strength of 36 , 000 Japanese troops deployed in the invasion of Singapore . Preparations . The 1st Malaya Infantry Brigade , comprising the British 2nd Loyal Regiment under Lieutenant Colonel Mordaunt Elrington , the 1st Malaya Regiment commanded by Lieutenant Colonel J . R . G . Andre , consisting of less than three sections of the Mortar Platoon , Anti - Aircraft Platoon with the Bren Gun Carrier Platoon under Captain R . R . C . Carter held in reserve . They were tasked with defending the approach to Pasir Panjang ridge , known as " The Gap " . The 44th Indian Brigade were on their right flank . A Malay platoon , consisting of 42 men , commanded by 2nd Lieutenant Adnan bin Saidi , was holding part of the defenses of Bukit Chandu . He and his men would take the brunt of the Japanese assault . Battle . The first battle between the Malay Regiment and Japanese soldiers occurred on 13 February at around 2 . 00pm . The Japanese 18th Division started to attack the southwestern coast along Pasir Panjang Ridge and astride Ayer Rajah Road . The Japanese 56th Infantry Regiment under Colonel Yoshio Nasu , supported by a considerable force of artillery , attacked the ridge during the morning . One of the units defending the line was B Company of the Malay Regiment . Under heavy fire from the Japanese , who were supported by artillery and tanks , B Company was forced to retreat to the rear . However , before the retreat could be completed , the Japanese succeeded in breaking through B Company ' s position . In the battle , the troops fought hand - to - hand combat using bayonets against the Japanese . A few from B Company managed to save themselves while others were captured as prisoners - of - war . This penetration led to the withdrawal after dark , of both the 44th Indian and 1st Malay Brigade , to the general line at Mount Echo ( junction of Ayer Rajah and Depot Road , around present - day Buona Vista ) . Bukit Chandu . On 14 February , the Japanese again launched a heavy attack at 8 . 30am , supported by intense mortar and artillery fire , on the front held by the 1st Malay Brigade . The defenders beat off this and a number of other attacks . The fighting included bitter hand - to - hand combat , and losses from both sides were heavy . At 4 . 00pm an attack supported by tanks eventually succeeded in penetrating the left , and the defenders on this flank were forced back to a line from the junction of the Ayer Rajah and Depot Road through the Brick Works and along the canal to Bukit Chermin . Owing to the failure of units on both its flanks to hold their ground , the 1st Malay Brigade withdrew at 2 . 30pm . It was at this point that C Company of the Malay Regiment received instructions to move to a new defence position , Bukit Chandu . Bukit Chandu ( means " Opium Hill " in Malay ) was named after an opium - processing factory located at the foot of the hill . This was also where C Company of the Malay Regiment made their final stand against the Japanese attack . Bukit Chandu was a key defence position for two important reasons . It was situated on high ground overlooking the island to the north ; and secondly , if the Japanese gained control of the ridge , it gave them direct passage to the Alexandra area . The British army had its main ammunition and supply depots , military hospital and other key installations located in Alexandra . C Company ' s position was separated from D Company by a big canal . Oil was burning in the canal , which flowed from Normanton Depot . The burning oil prevented C Company soldiers from retreating further south . The company was under the command of Captain H . R . Rix , a British officer . He encouraged the men to defend Bukit Chandu down to the last soldier , and was killed , together with many of his Malay Regiment soldiers in the last defensive battle at Pasir Panjang . The Japanese pressed their attack on Bukit Chandu in the afternoon , but under the guise of a deception . They sent a group of soldiers , dressed in Punjabi uniforms , passing themselves off as Indian soldiers in the British army . C Company saw through this trick as they knew that soldiers of the British army usually marched in a line of three whereas the disguised soldiers were in a line of four . When they reached the Malay Regiment ' s defensive line , C Company ' s squad opened fire , killing several men . Those who survived escaped downhill . Last stand . Two hours later , the Japanese launched an all - out banzai charge in great numbers . The attack overwhelmed the Malay Regiment , and the defence line shattered . Greatly outnumbered and short of ammunition and supplies , the Malay Regiment continued to resist the Japanese . Both sides engaged in fierce hand - to - hand combat using bayonets . Adnan bin Saidi was seriously wounded but refused to retreat or surrender and instead encouraged his men to fight to the end . Soon after , Pasir Panjang was under Japanese control , and Adnan bin Saidi , wounded and unable to fight , was captured . Instead of taking him prisoner , the Japanese continuously kicked , punched and beat him before tying him to a cherry tree and stabbing him to death with their bayonets . Casualties . During the entire Malayan Campaign , but mostly on 12 , 13 and 14 February 1942 in Singapore , the Malay Regiment suffered a total of 159 killed . Six of them were British officers , seven Malay officers , 146 other ranks and a large but unspecified number wounded . About 600 surviving Malay Regiment soldiers reassembled in the Keppel Golf Link area . Here , they were separated from their British officers . They later joined prisoners - of - war from the British Indian Army battalions at the Farrer Park concentration area . It remains unclear as to how many casualties the Japanese suffered . Aftermath . The battle of Pasir Panjang had little strategic significance . From a purely military operational perspective , the Battle of Pasir Panjang could not change the outcome of the fate of Singapore and it was a matter of time before the British would surrender to the Japanese 25th Army . The Allied units stationed there were simply tasked with defending the approach to the ridge , but instead had to resist the main invasion force . Opium Hill itself is situated on high ground overlooking the island to the north ; and it control the direct passage to the Alexandra area where the British army had its main ammunition and supply depots , military hospital and other key installations located in the Alexandra area . The fall of Opium Hill allow Japan access to Alexandra area , indirectly contribute to Alexandra Hospital massacre . Adnan bin Saidi is described by many Singaporeans and Malaysians today as a hero for his actions on Bukit Chandu — he encouraged his men not to surrender and instead fight to the death . In Singaporean and Malaysian school textbooks , he is also credited as the soldier who noticed the error in the marching style of the Japanese soldiers disguised as Indian troops .