World War Two battles around Hillview.

When World War Two descended onto Singapore in early 1942, the area that was to become Hillview in the future was still 'undeveloped' in the sense that we understand development today.

Located in the valley between the ridges of Bukit Gombak and Bukit Batok, the hill slopes were then covered mainly by rubber plantations on the Gombak slopes, while on the Bukit Batok ridge were remnants of old pineapple farms and some older gambier farms that had existed since the 1840s. This 'Hillview' valley stretch all the way from Bukit Batok hill north to the plains in front of what is the Ministry of Defence installation today. 

The only 'development' then in 1942 were the new factories of Ford Motors and the Hume Pipes Co., the more established Cold Storage Dairy Farm and the Nanyang Shoe factory at edge of Bukit Panjang Village. All these developments were along Upper Bukit Timah Road between the 8th & 10th milestones. Apart from these, it was mostly rubber plantations along the road.

It was an area that was still very ulu or rural, and at the periphery of the even more rural regions of Chua Chu Kang, Lim Chu Kang and Woodlands!

The invasion by the Japanese army towards Bukit Timah Village. 8-11 Feb 1942.
(click on the map for a detailed view)

The Japanese Invasion
On 8th February 1942, the Imperial Japanese Army invaded Singapore by crossing the Straits of Johore at the Sarimbun and Lim Chu Kang coast. 
Within the next 24 hours, the invading army had already conquered the entire Lim Chu Kang countryside and by afternoon the next day, 9th Feb, the British RAF Tengah airfield fell into their hands.

General Yamashita, the Japanese Army commander, who was nicknamed the Tiger of Malaya, had initially planned that the total conquest of Singapore would be completed by the 11th of Feb 1942.
However, his supply line was stretched too thin in Malaya and his army was running low on supplies, including food, fuel and ammunition by the time they had arrived at the Straits of Johore bordering Singapore.

Thus, he changed his immediate objective to the capture of Bukit Timah by the 11th of Feb instead.
Bukit Timah was where the British had their supplies, food stores and fuel depots and he coveted these supplies for his own men and army. 

Bukit Timah was also the highest point in Singapore which would afford the invaders a good view of the entire battlefield.
More importantly Bukit Timah was the major intersection where the main roads spread north, south and west of the island. Whoever controls the junction, controlled all movement to these areas.

With his objective set, his plan was to use two of his best army divisions, the 5th Division and and the 18th Division to capture Bukit Timah in a pincer movement. 
5th Division would moved along Choa Chu Kang and turn south at Bukit Panjang and head towards Bukit Timah with the support of Japanese tanks.
The 18th Division would move south-east through Bulim and along Jurong Road towards Bukit Timah Village, where they would converge with the 5th Division.
Both Divisions were given only 48 hours to accomplish this task of capturing Bukit Timah Village.

(There was a third Japanese Army Division called the Konoye Imperial Guards, but this unit was given a secondary task of moving across the Mandai and Thomson areas and played a more diversionary role to the main attack.)

Bukit Panjang
By the evening of the 10th Feb, the 5th Division had arrived at Bukit Panjang and was slowly maneuvering down towards Bukit Timah Village. They had fought and won fierce battles against the British at both Bulim Village and Keat Hong Village. By the time they arrived at Bukit Panjang, they also had the support of tanks which had been quickly pressed into service upon crossing the Straits of Johore.

At Bukit Panjang, the 5th Division was split into the three fighting regiments, the 11th, the 42nd and the 21st Infantry Regiments.
The 11th Regiment mauraded through Bukit Panjang Village and followed the water pipeline towards Bukit Timah via Dairy Farm, while the 42nd Regiment accompanied and provided infantry support for the tanks going down Upper Bukit Timah Road.

The 21st Regiment took the path along the Malayan Railway line and moved into the Hillview valley. This last group was given the task of capturing both the Ford and Hume factories.

Jurong
Over at the Jurong area, the 18th Division moved through the Bulim rubber plantations relatively easily till they came to Bukit Batok where they were met by the British Indian Army's 15th Infantry Brigade.
With their superior numbers and battle-hardened tactics, the Japanese forces routed the British army brigade at Bukit Batok.

Capture of Bukit Timah

By the late morning of the 11th Feb, both Japanese 5th and 18th Division had overwhelmed the British defenders at Bukit Timah Village and secure the high point of Bukit Timah hill.

Surrender
Following this victory, General Yamashita gave an ultimatum to the British to surrender.  However, the war in Singapore continued until for a few more days until the British finally surrendered on the 15th Feb, the first day of the Chinese New Year in 1942.
Three and half years of brutish Japanese Occupation was to follow for the citizens of Singapore.

For those who find this article TL;DR, I have actually done two videos on the same subject.
You can watch the video on Youtube at these links:-

Part 1. The Battle of Choa Chu Kang

Part 2. The Battle of Bukit Panjang

Further related links:-
Post-war history of Hillview