“The Japanese attack upon Hong Kong opened in the early morning of December 8 [1941] with action against the prepared positions of the British in the New Territories north of Kowloon. It was continued by the successful bombing of Hong Kong’s only airfield at 8:00 the same morning.

“The course of the siege thus opened may be divided into three periods. The first, that of resistance on the mainland, ended abruptly with the collapse of the British left flank and the subsequent withdrawal of all British forces across the harbor to Hong Kong Island, a movement which was completed by Friday, December 11.

“The second, that of the intensified bombing and shelling of the Island, was punctuated at its opening and its close by two Japanese peace missions offering to accept the Colony’s surrender – both of them being summarily rejected – and was marked by the deepening gravity of siege conditions, with the disruption of communications, widespread destruction, and the growing fear on the part of the authorities of large-scale fifth-columnist activities.

“The third period, that of the fighting on the island itself, opened on the night of Thursday the 17th with a successful Japanese landing at North Point, an operation which they extended and exploited throughout the following week, and closed when, on December 25, the defense collapsed and the Governor surrendered Hong Kong.

“Formal capitulation was effected on December 26, and the Japanese Army entered the city on the morning of the 27th.”

– Hong Kong under Japanese Occupation: A Case Study in the Enemy’s Techniques of Control, prepared by Robert S. Ward, American Consul, 1943

The Battle of Wong Nai Chung Gap (Hong Kong) propaganda postcard, 1942. Infantry of the Imperial Japanese Army seize an anti-aircraft artillery position. The Gap lies between Mount Nicholson and Jardine’s Lookout behind Wong Nai Chung (Happy Valley). It was a strategic passage between the north and south of the island, where five roads met. The capture of Wong Nai Chung Gap effectively split the British colony’s defense in two, hastening its surrender on Christmas Day 1941.

See also:
“Aleutian Operations” propaganda postcard, c. 1942.
Sinking the HMS Prince of Wales and HMS Repulse propaganda postcard, 1941.
Attack on Pearl Harbor propaganda postcard, c. 1942.

“The Battle of Wong Nai Chung Gap was the largest acretion of casualties in a single day, on both sides, in the whole [week long ground battle for Hong Kong] conflict. Its subsequent capture by the Japanese effectively led to the downfall of Hong Kong Island, splitting the forces there in two (separating the East/West Brigades).

“… On 18 December, the Japanese had landed around present day Taikoo and had made advances into the North Point area. They moved up towards Wong Nai Chung Gap from Braemar Hill … but also through Wan Chai and Happy Valley. Primary engagements occurred around the area of Jardine’s Catch-water, where there were two pillboxes manned mainly by Middlesex Machine Gunners (JLO1/2). Royal Scots on Mount Nicholson also became engaged in fighting the Japanese advance units on the adjacent Jardine’s Lookout, but also those coming up Happy Valley/Wan Chai area.

“The superior Japanese force soon closed in on the West Brigade HQ, before the staff and other units could be evacuated. The conflict ensued for a long period, with defenders holding out and inflicting heavy casualties through the use of heavy machine gun fire. The defenders were surrounded and pinned down, with few units able to get through to relieve them.

“The defense finally deteriorated after nearly every defender was either killed or wounded … Few stragglers managed to escape and the remainder of the soldiers (almost all wounded) were taken prisoner.

“The Japanese held the position against a number of counterattacks, and were able to effectively split the Commonwealth forces in Hong Kong Island. This was the key factor that led to the downfall of the colony and its surrender on 25 December, Christmas Day.”

– Wikipedia

Map: Offensive maneuverings of the Imperial Japanese Army, and the respective positioning of British, Canadian and colonial defense forces, Hong Kong Island, December 18-25, 1941. Wong Nai Chung Gap is located in the middle of the island (defended by the Winnipeg Grenadiers). [Source: Wikimedia Commons, public domain]