In the 1930s, the British army began installing defence structures at the gap as a strategically important location, being the primary passage between the North and South of Hong Kong Island.
Defensive structures included bunkers along Wong Nai Chung Gap Road, along with fortifications on Jardine's Lookout, near the end of Sir Cecil's Ride.
At the time of this Battle, the Wong Nai Chung Gap area included defenders of the Middlesex Regiment, The Winnipeg Grenadiers and the HKVDC.
They moved up towards Wong Nai Chung Gap from Braemar Hill through the primary use of Sir Cecil's Ride, but also through Wan Chai and Happy Valley.
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.