No Reason Why (Second Edition)

The Island


—18/19 December

Thursday, 18 December dawned fine and clear and the Japanese artillery and aerial bombardment increased in intensity. Although it still hit all parts of the Island, there was a very obvious concentration on the north shore. For what seems to have been the first time, the oil storage tanks at North Point were hit and set on fire, and other fires blazed on the north face of the Island. Fifth column activity also increased, Five West Brigade vehicles were destroyed by fire, and when the Canadian Service Corps men at Deep Water Bay commandeered twenty taxis that day, all but six were found to be inoperative due to sabotage. The Service Corps also reported that Japanese artillery fire made it very difficult to pass through the various gaps. 146-1

Of all the infantry units the most exposed to the Japanese fire and the most affected by it were the Rajputs, holding the eastern sector of the north shore. The state of the platoon holding Pak Sah Wan was described by the battalion's commanding officer as "exhaustion from perpetual enemy fire". 146-2 When Brigadier Wallis visited the Rajputs' headquarters that afternoon, "it was jointly appreciated that the long and persistent fire of all natures, air attacks and the heavy pall of smoke drifting across the waterfront were almost certain to prelude an attempt to land after dark." 146-3

There was little doubt that an attack was imminent and that it was coming from the north, yet Maltby and his brigade commanders made remarkably little attempt to alter their defensive positions to meet such an attack. The two Indian battalions on the north shore and the Middlesex in the pillboxes around the Island were presumably in the right position. Whether the position of the Royal Scots in Victoria was the best one possible for the Fortress Reserve, however, is open to question.

What of the two Canadian units, posted to meet an assault from the south that appeared increasingly unlikely?  

The Winnipeg Grenadiers were part of Brigadier Lawson's West Brigade. Lawson had established his headquarters in the vital Wong Nei Chong Gap in the centre of the Island. Three of the Grenadiers' companies were positioned to defend the west coast and western sector of the south coast-from east to west they were A,C, and B Companies at Little Hong Kong, Aberdeen, and Pok Fu Lam respectively. D Company, after its brief excursion to the mainland, was in position at Wong Nei Chong Gap to serve as a Brigade Reserve. Battalion Headquarters and Headquarters Company were at Wan Chai Gap just south of Victoria. Lawson had ordered three platoons formed from Headquarters Company to function as "flying columns", with two trucks per platoon. These stayed in the Gap during the nights and seem to have been the only mobile counter-attack force on the Island. As such, they might have been able to deal with an enemy reconnaissance party, but were woefully inadequate in the face of the invasion force the Japanese were about to fling at Hong Kong.

In East Brigade, the Royal Rifles were similarly strung out with a total battalion perimeter of 15 miles. Battalion Headquarters and Headquarters Company were beside Brigade Headquarters at Tai Tam Gap. Elements of Headquarters Company were, of course, with the other four companies as well. From north to south these companies were C at Lye Mun and Lye Mun Gap, A at Windy Gap and D'Aguilar Point, D at Obelisk and Red Hills, and B at Stanley View and Stone Hill. There appears to have been no provision for a Brigade Reserve.

At some time before the battle the Royal Rifles absorbed their first reinforcements directly into the battalion. A new platoon was now added to each company, identified by the suffix R, though whether these platoons consisted largely of reinforcements or whether the whole company was redistributed is unclear. In addition, Headquarters Company now disposed of several line platoons. The Winnipeg Grenadiers had absorbed their reinforcements as well, using some of them to fill vacancies created by the men who had not sailed on the Awatea. The remainder were absorbed directly into the companies, the majority going to Headquarters Company to enable it to form the "flying columns".

18 December seems to have held little out of what was now the ordinary for both battalions. In the Silesian Mission building at Sau Ki Wan in C Company area was Captain Banfill's Advanced Dressing Station. That day Major MacAuley, commanding Headquarters Company, visited Banfill and tried to persuade him to move as the location was so exposed. Banfill replied that as the Governor had refused to allow the women in the civilian first aid post to move, he did not feel that he could leave. 148-4 Other than this one attempt, there was little movement in East Brigade to counter the impending enemy incursion.

The Japanese had already completed their plans. Preparation for the invasion had commenced on 16 December with the organization of the landing forces and the issuing of plans to the various commanders. The three Japanese infantry regiments were to land on the Island in the same formation they had invaded the mainland, that is, from west to east, Shoji's 230th, Doi's 228th, and Tanaka's 229th. Each regiment would initially land two of its battalions, with the third being retained on the mainland as a reserve and for garrison duties. The 230th and 228th were to land between North and Braemar Points on the northernmost bulge of the Island, east of Victoria. After landing they were to swing right and advance westward over the northern half of the Island. The plan called for them to be south of the city of Victoria by daybreak of 19 December. The 229th would land further east on the north shore in the Aldrich Bay-Sau Ki Wan area and make a two-pronged thrust to the southern half of the Island, where it too would swing right and advance to the west. At some point, whether with the landing or after it, an engineering unit fighting as infantry, the Suzukawa Unit, was to take the right flank position and advance through Victoria. Although the Japanese had not attempted a landing in force on the Island before the night of 18 December, they had succeeded in landing at least one beach reconnaissance party of strong swimmers. The information gained by this group combined with pre-war espionage and plans captured on the mainland gave the Japanese a reasonably accurate idea of what to expect.

On the evening of 18 December, according to enemy accounts, the Japanese navy carried out a demonstration against the southwest coast in order to divert attention from the activities in the north. What form this diversion took is unknown, because nothing was noticed by the defenders.

Hong Kong Island - PM 18 Dec to dawn 20 Dec

By the time darkness fell, the weather, which had been clear earlier in the evening, had turned cloudy with occasional rain showers. Combined with the smoke from the burning oil tanks and other fires this weather made for an unusually dark night. The exact time of the Japanese embarkation and landing is uncertain-the British estimate is 8:30pm and the Japanese 9pm. The Japanese were transported in collapsible powered assault craft, assault boats propelled by oars, and commandeered civilian boats.

The full impact of the initial Japanese assault was to fall almost solely on the 5/7 Rajputs, who not only occupied positions along that section of coast, but also, for some reason, manned the pillboxes. In other words, approximately 700 infantry were supposed to defend almost three miles of coast, infantry that had been bombed and shelled almost incessantly for the last five days, and as the dark night and the smoke made it almost impossible to locate the crossing Japanese, even with the few searchlights remaining intact, it is no wonder that the Rajputs did little more than inconvenience the Japanese and inflict moderate casualties. British artillery did not intervene until after the first landings, and then with little effect as there were no Japanese in the target area at Quarry Point. All three Japanese regiments were somewhat disorganized after a water crossing under fire on a dark night, but each reached its designated landing area. As soon as the first waves of invaders reached the shore, they closed with the defenders. The 5/7 Rajput Regiment disintegrated. Some elements, particularly the officers and NCO's, put up a fierce resistance, and died to the last man. Almost half the battalion was composed of partially-trained recruits, and the strain of the previous days and the shock of the Japanese assault proved too much for many of them. Among the Canadians to report on this unfortunate unit was Captain Banfill, who stated that the Rajputs put up a good fight in isolated areas, but eventually broke and ran. The diary of C Company of the Royal Rifles recorded: "Between 2100 and 2200 hours there was a continual road race of Indian Troops running past without arms in the direction of Tai Tam. No information could be obtained from them, they would only say, 'Japs, thousands of Japs.’” 150-5 The early hour indicates that they had not put up a prolonged resistance. With the exception of a single company on the left flank that had not been engaged and a handful of stragglers, the 5/7 Rajputs took no further part in the defence of Hong Kong.

East Brigade-8pm, 18 December*

*As the battle for the Island developed, it evolved into two separate conflicts, one fought by East Brigade and one by West Brigade. The narrative will alternate between these two sections of the battle.

After the hapless Rajputs, the next infantry encountered by the oncoming Japanese was C Company, Royal Rifles of Canada. This was the most northerly of the battalion's companies. It was stationed in Lye Mun as a "Reserve and Security Force", but seemed destined to be in the forefront of the battle. Also, as in the case of the Pak Sah Wan "landing" of 15 December and the wooden gun episode, it tended to become involved in off-beat occurences and Major Bishop could not seem to get "on net" with Brigadier Wallis. The night of 18 December was to see this continued.

Despite the fact that he anticipated being relieved at 9pm by D Company, at 8pm Major Bishop, concerned at the weakness and exhaustion of the Rajput platoon at Pak Sah Wan and unaware that the Japanese were even then entering their boats, sent 15 Platoon under Lieutenant Scott forward to reinforce the position. Moving up, Scott and his men at 8:30 ran into a band of armed men in civilian clothes at the Lye Mun gate. There was a brief flurry of shots and bayonet thrusts. Scott held his ground and reported the incident to Bishop, who ordered the platoon to pull back to Lye Mun Barracks. Accompanied by Rifleman Gray, Bishop then left Company Headquarters at the Lye Mun Gap and made a personal reconnaissance. Moving up to Sai Wan Fort on Sai Wan Hill above the Gap, he encountered a party of artillerymen under a corporal who reported that the fort was now occupied by Japanese dressed as coolies, who had chased them out without even one shot being fired. The fort had indeed been occupied, although whether they were fifth columnists or Japanese in civilian clothes is uncertain. Being unable to contact the Rajput Commanding Officer (who probably had enough on his mind already) Bishop decided to deal with the matter himself and reported the capture of the fort to Battalion Headquarters who passed the information on to Brigadier Wallis. The Brigadier immediately telephoned C Company Headquarters and told Bishop, "there is no such thing as the enemy being at Fort Sai Wan. There are Canadians in the Fort." Bishop informed him that, as commander of the Canadians in the area, he could state that there had never been Canadians in the fort-indeed, he had not been allowed inside the place himself. Wallis assured him, "I have definite information that there are friendly troops in the Fort." Bishop replied, "They don't act friendly. We are being raked by automatic fire from there this moment." He added that he was organizing an attack on the fort at once. 152-6

Wallis undoubtedly thought that Bishop was unreliable, although he had done absolutely nothing wrong and was merely reporting the loss of a position by another unit and preparing to act. By this time it had become obvious that more was going on than a mere fifth column coup. Further to the north 15 Platoon had been attacked and pushed out of Lye Mun Barracks. Inspecting the bodies of a Japanese patrol they had cut down, 15 Platoon found three in uniform and four dressed as coolies. 14 Platoon at Sau Ki Wan had come under heavy attack from the left, been forced to extend its line to avoid being outflanked, and finally drew back to Company Headquarters. The Company had already been inundated with fleeing Rajputs. Bishop asked for reinforcements and artillery support to stage a counter-attack. This was referred to Brigade which refused permission to reinforce Bishop, but did provide an artillery barrage on call. Bishop, determined to at least get back the fort as it dominated most of his position, detailed 13 Platoon to go in from the northeast where the slope was gentlest, but at that moment a Captain Bumpas [or Bompas], Royal Artillery, arrived from Brigade Headquarters. Saying that he had "secret plans", he took charge of the attack and switched it to the east side, where the fort had a 20-foot perpendicular wall. The attack, now involving 15R Platoon as well, started and Bumpas stayed on the road, "Brandishing a revolver and shouting that he would shoot any men who attempted to retire." This was a rather inappropriate threat, as the only people who had retired from the area that night were the Royal Artillery. Major Bishop advised him to shut up and lead the attack if he was so bloodthirsty, but at this point Bumpas' enthusiasm wore off. He ordered Captain Gavey to stop after the enemy was driven into the fort, saying "we will take the Fort at dawn, according to plan". 152-7 The abortive attack had cost the company 9 men killed, and Captain Gavey was seriously wounded while attempting to disengage. During the attack, Bishop asked Brigade to have the Mount Collinson searchlight turned onto the fort, but was told the light came under another command. As the attacking force was retiring, however, the light did come on, giving the Japanese excellent targets. The entire fiasco was to set the scene for relations between East Brigade Headquarters and the Royal Rifles for the rest of the battle.

While C Company was being drawn into battle, there were various changes of position within the battalion. D Company was due to relieve C Company that evening, but the relief was cancelled and D Company stood fast except for 17 Platoon. This was ordered north to Battalion Headquarters at Tai Tam Gap and thence to a position at a ration store halfway between Lye Mun and Tai Tam to act as a second line of defence if C Company's front line fell back. A small party from A Company was ordered to Boa Vista at 9pm, B Company sent 12 Platoon up to Tai Tam Gap at 11:30pm, and Headquarters Company sent 5 Platoon and two sections from 3 Platoon, all under Lieutenant Williams, to Mount Parker.  Mount Parker was the dominant feature immediately south of the Lye Mun area, and the force from the Royal Rifles was intended to reinforce a platoon of Volunteers that was holding the area. The Volunteers chose to believe they were not being reinforced, but relieved, and all disappeared except for an NCO and two men. The fact that they remained may indicate that the misinterpretation by the others was deliberate.

From midnight on, all of C Company was under heavy and continual attack by the advancing Japanese, who were from Tanaka's 229th Regiment. One of Tanaka's two battalions, the 3rd, had landed at Aldrich Bay and was heading for Mount Parker while the other, the 2nd, had landed further to the east and was moving south toward Sai Wan and the Tai Tam Gap. Major Bishop's men were the first serious resistance the 2nd Battalion had yet met, and it must have come as an unpleasant surprise. C Company possessed unusually heavy firepower-in addition to its own weapons it had acquired two Lewis guns, a Vickers machine-gun, and an extra Bren, presumably from decamped Volunteers or artillerymen. In addition, every officer had contrived to get his hands on a Thompson gun. As the Japanese advanced, the fiercely-burning fires in Sau Ki Wan threw them into relief, and they suffered severe losses. One Japanese officer told the Canadians after the capitulation that his company suffered 65% casualties in this action. C Company stopped Tanaka's 2nd Battalion dead in its tracks, forced the abandonment of its plan to head south for the Sheko Peninsula, and deflected its thrust to pass along the western slopes of Mount Parker toward Repulse and Deep Water Bays.

At 1:30am Captain Bumpas, apparently still on the scene, informed Bishop that his company should retire as the enemy was circling to the rear and isolating them. Whether Bumpas was in touch with Brigade or not, his statement about the positions was undoubtedly true. The Japanese, unable to get past C Company, were moving around its left flank. By 2:45 each platoon had reported that it had successfully disengaged and was moving back to where Lieutenant Power was waiting with D Company's 17 Platoon. This withdrawal was difficult and slow as the wounded could not be left behind, and, at intervals, the platoons had to overlap and cover each other. The success of this is particularly notable when it is recalled that these men had not had a hot meal in five days, had manned their positions continuously under heavy shellfire for the same time, and had slept only in weapon pits. Men were falling down asleep wherever they stopped.

When the company reached its destination it was realized that two wounded men had been left at Lye Mun. Major Bishop, Lieutenant Scott, Sergeant Clayton, and a signaller went back through the advancing Japanese and after a sharp skirmish brought the men away. There is no question that, in the first hours of battle for the Island, C Company of the Royal Rifles put in a performance that few units anywhere could have equalled.

The withdrawal of C Company, though militarily the only course of action, left all remaining personnel from any unit at the mercy of Tanaka's men. Earlier that night when the Japanese had overrun the Volunteer anti-aircraft position on Sai Wan Hill, they took twenty prisoners and bayoneted them. Only two miraculously survived their wounds.

By dawn on 19 December Captain Banfill's Advanced Dressing Station was deserted, except for a few personnel from it and the civilian first aid post. They had just finished treating two badly wounded Rajput officers who had been shot on their retreat south,* when a party of Japanese occupied the building and led the men away, subsequently murdering all but four of them. The women were held for several hours and then released.

*These officers claimed to have been shot by Canadians and this story became widely circulated. Banfill did not believe this, with good reason, as the only Canadians had long since withdrawn. Presumably the Rajputs, moving through an area formerly held by the Canadians but now swarming with Japanese, were shot unexpectedly and leapt to the wrong conclusion.

While C Company was in its new position halfway between Lye Mun and Tai Tam Gap the Company Quartermaster Sergeant issued badly needed ammunition and the Royal Rifles Adjutant, Captain Atkinson, came up with some hot food and was asked about the counter-attack Bumpas had talked about. "Captain Atkinson when questioned replied that there did not appear to be any plan as far as Brigade HQ was concerned re counter-attack, and doubted if ever there had been one." 155-8 Certainly there was no concerted plan for the Royal Rifles in the early morning of 19 December, as shown by the confused and futile battle for Mount Parker.

As Mount Parker was now held by only a single platoon plus two sections from another, the detached party from A Company (Lieutenant Blaver plus 20 men) which had originally been intended to hold 5 Platoon's vacated position was sent to Mount Parker as reinforcements. Then at 3am, Captain Clarke from Headquarters Company was ordered to take D Company's 16 Platoon (which a few hours earlier had been ordered up to Boa Vista), proceed to Mount Parker, take command, and co-ordinate the defence. In the meantime, the guide leading Blaver and his men had taken a wrong turn and they did not reach their objective until 7:30am. They found that the Japanese had possession of the crest and were assaulting the defence positions. From his position on the lower slope Blaver could see well over a hundred enemy but nevertheless he and his twenty men attempted an attack. They were hit by machine-gun fire from their right while the Japanese 100 feet above them on the crest of Mount Parker lobbed down grenades. After ten casualties they gave up the struggle and withdrew down the mountain. Firing continued on the crest until 8:30am at which time the last defence position must have been overrun. By this time Captain Clarke, making a personal reconnaissance from a ridge 500 feet below the crest, had seen Blaver and his men in their hopeless struggle. Clarke returned to Boa Vista, where he had left 16 Platoon, and telephoned Brigade. When Brigadier Wallis asked if Mount Parker could be retaken, Clarke replied that he didn't think so, but would try if reinforced. 155-9 Two additional platoons, one from B and one from D, were ordered up, but before the attack got underway it was cancelled. This is fortunate-all of Tanaka's 2nd Battalion was in the Mount Parker area and it is doubtful if a co-ordinated attack by the whole Hong Kong garrison could have ejected them. It would have been madness for three Canadian platoons to try.

Aside from the Mount Parker fighting, the only other early morning activity was a desperate attempt by Major MacAuley to reach Captain Banfill. The attempt failed but MacAuley did return with a truckful of wounded. Mortar fire was also brought down on the northeast slopes of Mount Parker.

It was decided some time in the early morning (whether by Battalion or Brigade is uncertain, but probably the latter) to bring A and B Companies forward to join Headquarters Company at Tai Tam Gap. B Company reached Tai Tam Gap at 8:30 and took up defensive positions there.

By 9:30am Brigadier Wallis had had time to take stock of the situation. As the Rajputs had been annihilated, his only effective infantry unit was the Royal Rifles. The Rifles had effectively blocked the Japanese thrust along the low ground from Lye Mun to Tai Tam, but the Japanese had seized the high ground to the west. As there seemed no hope of organizing a co-ordinated counter-attack from the Rifles' present positions Wallis decided to concentrate his infantry and mobile artillery in the area around Stone Hill and Stanley Village, from where they could be used to best advantage.

Before issuing the order Wallis discussed the matter with Maltby, who had hoped instead that East Brigade be moved to the west to link up with West Brigade. Wallis did not think Maltby appreciated the nature of the terrain nor did Wallis consider the Royal Rifles capable of the move across the enemy-held high ground. He recalled later that it was at this time that "I realized that the Battalion was incapable of real fight". 156-10 As the only fighting Wallis had to base this opinion on was the successful fight of C Company against a whole battalion and the failure of a small party of men to drive another battalion off Mount Parker, it is obvious that he had failed to grasp the realities of the situation.

Orders for the move went out around 10am and, after various trials and tribulations, all Royal Rifles companies reached their new positions. Most of D Company was at Stanley Mound by dark; C Company was pulled back to Tai Tam Gap at 10:20am and had taken up defence positions at Stanley View by nightfall. B Company covered the withdrawal of the others and so had to take up its positions on Sugarloaf Hill in the dark-a difficult task as no path could be found. Headquarters Company personnel stayed to the last, evacuating company stores, covered by a single platoon of B Company under Lieutenant Ross. Tai Tam Gap was finally evacuated at 4:45pm.

During the last 45 minutes Ross and his men were continually under fire from almost 200 Japanese who were trying to surround the abandoned position. Eventually, Headquarters Company and Battalion Headquarters moved into Palm Villa, on the coast near Tai Tam Bay. It had been a particularly frustrating day for A Company. At 7:30 the company was ordered out of its positions at D'Aguilar and told to move up to Battalion Headquarters at Tai Tam Gap. They moved off with their only truck at 7:50am and were half a mile up the road when the order was cancelled. No sooner had they arrived back at D'Aguilar than they were ordered up again. On arriving at the Gap at 10:30 they were immediately instructed to move south to Stanley Mound, but halfway there Brigadier Wallis ordered Major Young to halt and march his company to Stone Hill, as all plans had changed and the force was going to "counter-attack the enemy and drive him back into the sea". There was no counter-attack, but the exhausted company was finally deployed around Stone Hill by 6pm.   157-11

Whatever problems he might have had with the Royal Rifles, Brigadier Wallis had reason that day to think them paragons compared with his artillery. The coast defence guns at Cape D'Aguilar and Cape Collinson were supposed to continue fighting after the infantry had pulled back, but instead the guns were destroyed and abandoned. Even worse was the situation with the mobile artillery. When Wallis ordered one of the batteries to "get out of action" and leave, the gunners accidentally or deliberately took this as an order to put the guns out of action. Another battery stayed in action too long and lost the guns. As a result, the only mobile artillery left to East Brigade was one 18-pounder and two 3.7-inch howitzers.

The first day's fighting had been disastrous for East Brigade. The infantry force was halved, the artillery was nearly wiped out, and the whole force was concentrated in a small area of the south coast. The Canadians of the Royal Rifles were tired, but not disorganized, though they had suffered casualties. Nearly two platoons had been lost in the Mount Parker battle, and of the 177 men with C Company on 18 December, only 68 answered roll call at Stanley View the next evening.

West Brigade

The fight in the West Brigade area, even more than that to the east, was dictated by the ridge of mountains running east to west along the Island. In the eastern half of the Island the high points are, from east to west, Mount Parker, Mount Butler, and Jardine's Lookout, with the latter in the area assigned to West Brigade. On the west side of the Island, separated from Jardine's Lookout by Wong Nei Chong Gap, are, from east to west, Mount Nicholson, Mount Cameron, Mount Gough, and Victoria Peak. Therefore, when Brigadier Lawson located his Brigade Headquarters at Wong Nei Chong Gap, he had chosen not simply a strategic location from the point of view of control and communication, but what was probably the prime Japanese objective of the early stage of the invasion. Indeed, Lawson seems to have belatedly realized that the position, while admirable for control, was far from ideal defensively. On 18 December Major Lyndon, the Brigade Major, located a new site for Brigade Headquarters at Black Links, to the south of Mount Nicholson. The move was scheduled for the following day.

When Colonel Shoji's 230th and Colonel Doi's 228th Regiments landed near North Point and Braemar Point respectively, their initial experiences were much the same as Colonel Tanaka's. A certain amount of trouble was caused by the Rajput defences, but this was quickly dealt with, and both units headed inland. Unlike Tanaka's Regiment, both units advanced directly to the high ground and, skirting Braemar Hill, drove south toward Jardine's Lookout, overlooking Wong Nei Chong Gap, and to the Gap itself. Shoji's 2nd Battalion was to take Jardine's Lookout and his 3rd was to occupy the Gap. Doi had some communication problems, but his account indicates that his unit arrived at the foot of the Lookout at first light, took that position, and proceeded on to the Gap. The Lookout was held by two platoons of Volunteers. Some of their pillboxes were quickly overrun by Shoji's men, but others, on the southeast slope, held out until the afternoon.

The first action taken by Brigadier Lawson in response to the Japanese landings was to order the three Grenadier flying column platoons forward from the Gap to oppose any Japanese breakthrough. One platoon went to a road junction northwest of the Gap while another, under Lieutenant Birkett, was ordered to Jardine's Lookout and the third, under Lieutenant French, to Mount Butler. There had been a Japanese breakthrough, but in much greater strength than could be contained by such small bodies of troops. As in the battle on Mount Parker, Birkett's and French's platoons had as much success as one might expect of platoons sent to attack oncoming battalions. French's platoon found the Japanese already occupying Mount Butler and, failing to dislodge them, pulled back. French was wounded, and then killed, covering this withdrawal. Birkett's platoon did not reach its objective until just before dawn. It, too, encountered an overwhelming number of enemy and was attacked. Birkett was killed while trying to cover his men with a Bren gun. Some of the survivors of his platoon reached the remaining Volunteer pillboxes and played a large part in enabling them to hold out until the afternoon.

Brigadier Lawson realized shortly after midnight that some of the enemy had penetrated as far as Mount Butler. D Company of the Grenadiers, which had been designated as Brigade Reserve, was holding positions in and north of the Gap. Not wishing to leave the Gap exposed by moving D Company, Lawson brought up A Company less one platoon from Little Hong Kong village. At 2:30am he ordered the Company Commander, Major Gresham, to take A Company plus one platoon of D Company (to replace the A Company platoon left behind), clear Jardine's Lookout, and, it would seem, occupy Mount Butler (although this last order is not recorded). The company did not reach its objective until dawn. A Company's last battle, though it resulted in the award of the only Victoria Cross of the Hong Kong fighting, is wrapped in obscurity, largely due to a lack of reliable witnesses and some ambiguity in Japanese records. The evidence indicates that the company did reach Mount Butler at dawn and cleared it of the enemy. A series of heavy Japanese counter-attacks forced the Canadians to withdraw in the late morning, and by mid-afternoon they were surrounded before they could complete their withdrawal. By the end of the fighting, almost the entire company had been killed, wounded, or taken prisoner. During their last stand, Company Sergeant Major J.R. Osborne, who had been a pillar of strength throughout the entire action, deliberately covered a grenade with his body, saving the lives of those of his men within its range at the cost of his own. After the war he was awarded a posthumous Victoria Cross.

It is difficult to fit this fierce little battle into the context of the Japanese accounts, which contain few details. Neither regimental commander mentioned fighting on Mount Butler, yet both claim to have taken Jardine's Lookout. However, control and communication that night and early morning was as difficult for the Japanese as for the defenders, and as the two features are very close together and part of the same hill system, a mistake could easily have been made, particularly in the fog and mist. Shoji mentions in his account that resistance from the Indian (that is, Volunteer) defenders was "slight", but at another point states that strong resistance was encountered on the Lookout. Shoji also recounts that as he was moving up "fierce rifle fire [was] heard from the direction of 2nd Battalion moving toward Jardine's Lookout," 160-12 which sounds more like an attack on a company than on pillboxes or platoon positions (though it may have been Lieutenant Birkett and his men). Among the possibilities are that Colonel Doi's men attacked Mount Butler thinking it was Jardine's Lookout, that some of Shoji's 2nd Battalion did the same, or that some or all of A Company's gallant fight was actually on the Lookout.

At the same time as Colonel Shoji heard the firing from the direction of the Lookout he also heard the commencement of a similar heavy engagement in the direction of Wong Nei Chong Gap. Shoji's 3rd Battalion had made contact with 17 and 18 Platoons of the Grenadiers' D Company, which were in positions north of the Gap. After a fierce fight against vastly superior numbers both platoons were surrounded and overrun. A few men managed to escape over the rough country. The attacking force then headed for the Gap, and was soon joined by the bulk of the 2nd Battalion which Shoji diverted from Jardine's Lookout. Doi's 1st Battalion was also at the Gap and in action by daylight, and by the end of the day, no less than four Japanese battalions were attacking the Gap and the slopes above it.

By first light Brigadier Lawson must have been sickeningly aware of the precarious situation of both his Brigade Headquarters and the vital Wong Nei Chong Gap. A Company of the Grenadiers had vanished without trace into the hills, and one platoon of D Company with it. Once the two forward D Company platoons went under there was only D Company Headquarters, Brigade Headquarters, and the headquarters of West Group of the Fortress Artillery. On both sides of the Gap steel-doored anti-aircraft shelters had been dug into the cliff. D Company Headquarters occupied those on the west side while Brigade and Artillery Headquarters were on the east. One reinforcement, consisting of Lieutenant Blackwell and 20 Grenadiers, reported to D Company Headquarters at 7am. These men had originally been detached from Headquarters Company to guard the coast at Belcher's Bay. They were ordered to man a pillbox further up the Gap, but before they could set out the Gap came under heavy attack so they remained and fought from D Company Headquarters. This little group was to make a stand of epic quality. They were well-equipped with Bren and Thompson guns, had plenty of ammunition, and, as long as they held their positions, the vital Gap could not be passed. The Japanese account describes how their first troops "came upon a powerful group of sheltered positions... The enemy fire from these positions was so heavy that not only was the advance balked, but our troops were thrown into confusion. " 161-13

The morning was marked by a succession of attempts to relieve or reinforce the Gap. At 7am Brigadier Lawson requested a company of Royal Scots to attempt a breakthrough to the Gap. A heroic but futile effort was made by A Company, but the Scots came under Japanese fire which destroyed their trucks. Although they made a gallant effort to press on, less than a dozen reached the Gap, and the rest of A Company, now reduced to fifteen, was forced to fall back. Three naval platoons suffered the same fate. These men, from the disabled HMS Thracian, were on their way to Little Hong Kong to occupy the former Grenadier A Company positions but were instead ordered to clear the Gap from the south. They were ambushed before they could get out of their trucks, and lost most of their men without accomplishing anything. The remaining platoon from the Grenadiers' had earlier been despatched to establish a road block in the area of Tai Tam. Failing to reach their destination before the Japanese, they returned to Wong Nei Chong Gap to find it under attack. The platoon made several attempts to clear positions to the front and flank, but only succeeded in losing men. Around 1pm the survivors withdrew to Battalion Headquarters.

In the meantime the sands had run out for Brigadier Lawson. By 10am the Japanese had surrounded Brigade Headquarters and, unlike D Company Headquarters, the defenders did not have the firepower to keep the enemy at bay. After destroying essential records and the telephone switchboard, Lawson and his staff emerged from the shelter. Major Lyndon had earlier telephoned Fortress Headquarters that they were going to evacuate to the new Headquarters position at Black Links chosen the previous day, but Lawson had subsequently told Wallis that they were going outside to fight it out, presumably because Japanese proximity prevented a successful evacuation. Japanese fire commanded the Gap, and as Lawson's group entered the killing ground the Brigadier was hit and fatally wounded. The Japanese found his body several days later and buried it with honour.

D Company Headquarters continued to resist the enemy. Their numbers were slowly augmented by stragglers and survivors, mostly from the Grenadiers but some from other units. These reinforcements balanced the losses in killed and wounded. No other reinforcements ever arrived. Captain Bowman of D Company led a counter-attack to clear the enemy from the front, where they were making gains. This attack achieved a temporary success, as Bowman's group got above the Japanese and forced them to retire. But it could not last, and Bowman was killed while withdrawing to the shelters, whereupon the Japanese re-occupied their positions.

Realizing that Lawson was, if not dead, at least not in a position to effectively command the Brigade, Maltby ordered a major counter-attack by West Brigade to halt the Japanese, clear the Gap, and link up the two brigades.

In the north the Punjabs, who had already made one unsuccessful counter-attack against the Suzukawa Engineering Unit at Caroline Hill just east of Leighton Hill and suffered 30 killed and wounded, were to attack east toward the North Point Power Station. This was still held by a party of Volunteers (including the group over military age) and other defenders with exceptional courage and determination against a number of Japanese attacks. The Punjabs do not seem to have received the order and the Power Station fell late that afternoon.

The Royal Scots were ordered to attack south to clear Jardine's Lookout and the Wong Nei Chong Gap. One company was to circle around Mount Nicholson and attack northward and the other two to head straight toward the Gap. These two companies came under fierce Japanese fire at the same point where A Company of the Royal Scots had been all but annihilated that morning. They suffered severe casualties and dispersed to wait for nightfall before continuing their advance.

The Winnipeg Grenadiers' contribution to this general advance was to be an attack by Headquarters Company, led by Major Hodkinson, who at 2pm was ordered to counter-attack at Wong Nei Chong Gap, clear the area, and proceed to Mount Parker! Between the support detachments which had been attached to other companies, Lieutenant Blackwell's 20 men now fighting with D Company, and the heavy losses in the flying column platoons, only 40 men could be found. A platoon of C Company was brought up from its position at Aberdeen and arrangements were made for A Company of the Royal Scots to participate. It is uncertain if either Hodkinson or Fortress Headquarters was aware of the hideous losses suffered by this unit that morning. As the Royal Scots failed to arrive on time, Hodkinson began the attack solely with his few Grenadiers. He detached a platoon under Lieutenant Corrigan to provide flank protection from Mount Nicholson. Corrigan's platoon fought its way to the top of Mount Nicholson, arriving with only five men unwounded, continued down the far slope above the Gap, and engaged the enemy until nearly midnight, by which time the ammunition was exhausted. Meanwhile, Hodkinson and the main force were continuing around Mount Nicholson on the Black Links Road when they came upon approximately 500 Japanese eating. The enemy's security must have been exceptionally poor as the Canadians achieved complete surprise and poured in accurate fire, dispersing the enemy with many casualties. This force was probably Shoji's 3rd Battalion. After this clash the Grenadiers pushed on until close to the junction of the main road where, at approximately 5pm, they were joined by the remnants of A Company of the Royal Scots, their fighting spirit still high despite the morning's ordeal. The party then split up, with Hodkinson and four men going across country to approach the Gap from the north and take over the old Brigade Headquarters, while Lieutenant Campbell cleared the Gap from southwest and west. On the way, Hodkinson's little group re-captured a Vickers machine-gun post. The assault was well co-ordinated, and the Gap was cleared by Campbell's men, aided by some good grenade throwing by Hodkinson. They made contact with the Grenadiers' D Company Headquarters, which at this time consisted of twenty wounded and seven unwounded men still holding out in the shelters. Hodkinson reported his successes to Battalion Headquarters which passed the information on to Fortress Headquarters. The latter then ordered Hodkinson's party to move south through the Gap, capture the police station which was built on a commanding knoll at the south entrance, and then proceed to Mount Parker "even without any artillery preparations". 163-14 It is difficult to judge which is the most incredible, the order given by a Headquarters that obviously did not have the slightest grip on reality, or the little group of men actually undertaking to carry it out. Hodkinson's force, now consisting of two officers and 24 other ranks, commenced an attack from the flank on the police station at 8pm. They charged up the hill to the station under heavy defensive fire and, when about 1/4 of the way up the hill, about forty Japanese appeared on the skyline and lobbed a volley of grenades. Most of the attackers became casualties, including Hodkinson, who was seriously wounded. A small party under Sergeant Patterson was left to try to hold the position, but the attempt failed, and Patterson was killed. Thus ended possibly the most gallant and successful attack against the greatest odds of the entire battle.

The next force to approach the Gap was a small group of Indian artillerymen and two Volunteer armoured cars despatched from East Brigade. They approached the Gap from the south, reported the police station cleared (which seems strange, in view of the prior experiences of Hodkinson's men and the later experiences of the Royal Scots), and, coming under fire, dispersed.

Early the next morning, before dawn, the Royal Scots put in two attacks, each pushed home through fierce fire with great courage, great losses, and no success. The first assault was by the two companies to the north, straight through the Gap as far as the police station. The other was in conjunction with the company that had come around the south of Mount Nicholson. Two-thirds of the Royal Scots became casualties on 19 December and, at first light on the 20th, the remnants of two companies were in positions on the northeast slopes of Mount Nicholson and the other at the bottom of the southern slopes.

The day had not gone as badly for West Brigade as for East. West Brigade had not yielded as much ground, and two of its battalions, the Punjabs and Middlesex, had not faced the full force of the Japanese infantry. However, its Headquarters had been annihilated, the Royal Scots had been reduced to a fraction of its former self, and A, D, and Headquarters Companies of the Winnipeg Grenadiers had been almost wiped out.