Jardine's Lookout was the sight of fierce conflict in the Battle of Hong Kong and particularly, the Battle of Wong Nai Chung Gap. The Hong Kong Volunteer Defense Corps and Middlesex Machine gunners manned two pillboxes and other areas defending the pass around Jardine's Catchwater, as well as Canadian Winnipeg Grenadiers defending the adjacent Mount Butler. Japanese forces, after landing on the North Shore of Hong Kong Island; used Sir Cecil's Ride and moved up to this pass midway up the lookout and were engaged by Commonwealth forces. The fighting was the preliminary conflict in the Battle of Wong Nai Chung Gap.