The 1st Parachute Battalion, having abandoned its original objective of seizing the high ground to the north of Arnhem, moved in a south-easterly direction during the night until they arrived on the Utrechtseweg; the 3rd Battalion's "Tiger" Route. It was well known that the Germans disliked fighting in darkness, and as such the Battalion, with Major Stark's "S" Company in the lead, made excellent progress before dawn and passed through Oosterbeek unhindered. At 05:00, to the east of the town, they met determined opposition whilst trying to pass beneath a railway bridge. No.7 Platoon suffered heavily during the subsequent exchange of rifle and mortar fire, losing seven men killed, several more wounded and two prisoners. Major Stark was about to attempt a flanking attack with his remaining two platoons when, owing to the strength of the enemy and his unwillingness to become further delayed by such actions, Lieutenant-Colonel Dobie ordered "S" Company to disengage. "T" Company took over the lead and guided the Battalion south in the hope of forcing an easier passage along the "Lion" Route, which had been so successfully used by the 2nd Battalion on the previous day.
After resting overnight, the 3rd Battalion resumed their advance at 04:30. The road ahead was believed to be held in strength by the enemy, so Lieutenant-Colonel Fitch decided to side-step this opposition by moving his Battalion onto the lower "Lion" Route. Like the 1st Battalion they made swift progress in the darkness, and by 07:00, "B" Company, who were in the lead, had entered Arnhem and were only a mile short of the Bridge. Resistance ahead of them was believed to be slight at this time, however it was here that they were forced to halt as they had outrun the remainder of the Battalion. Following in their wake were "A" and Headquarters Companies, included amongst which were all of the Battalion's mortars, Vickers machine-guns and most of their anti-tank guns, and since dawn they had been harassed by German snipers and machine-gunners to such a degree that they had lost sight of Lieutenant-Colonel Fitch and "B" Company. These two halves of the 3rd Battalion were not to be reunited as those in the rear did not know where "B" Company were and so ended up taking a different route.
With only "B" Company and a few attached engineers at his disposal, Lieutenant-Colonel Fitch could do nothing but wait, and he was still burdened by the presence of Brigadier Lathbury and Major-General Urquhart. German troops spotted the Company during the morning but did not mount a serious challenge. Instead, using armoured vehicles and small numbers of infantry, they were able to hold the paratroopers in an awkward stalemate for six hours, until they were finally able to slip away in the darkness; the surrounding terrain being very difficult to negotiate under such conditions in broad daylight.
It was in the afternoon, however, Major-General Urquhart decided that he had to attempt to break-out and make his way back to his Headquarters as the fate of the battle was hanging in the balance. With just Lathbury and two other officers for company, he set out through the dangerous streets of Arnhem, which were by now well covered by enemy patrols. After making slight progress, the party came under machine-gun fire and Lathbury was wounded. His fellow officers took him into a house, at the request of the Dutch occupants, where it appeared, wrongly in fact, that the bullet had struck his spine and left him paralysed. Lathbury urged the General to press on without him, and as they were about to do so a German soldier appeared at the window and Urquhart shot him dead.
The three men set off once more but German patrols were everywhere and they were unable to make any progress. Fortunately, another Dutch couple urged them to shelter in their attic. It was with great reluctance that Urquhart accepted this offer, because the Division was effectively blind at this time as those back at Divisional HQ could only guess at what was happening in Arnhem. Urquhart knew that the situation might be transformed if only he could get back, however this was now impossible as the house in which he hid had been surrounded by German troops; all of whom were completely unaware that the British Divisional Commander was only a few yards away. Urquhart had no choice but to wait until British troops broke through to Arnhem in strength.
The 1st Battalion, meanwhile, had made their way down onto the "Lion" Route and were drawing near to the same railway bridge that "B" Company had successfully passed through earlier. It was here that they encountered those elements which had become separated from the 3rd Battalion, and Lieutenant-Colonel Dobie was only too happy to take these under his wing, not least because his own "R" Company, with whom were also most of his heavy support weapons, had still not rejoined the Battalion after being delayed in fighting around the Amsterdamseweg on the previous day. At 08:00, the 1st Battalion arrived at the railway bridge but found that it was strongly held by German infantry and armoured vehicles. With no other way through to Arnhem, the Battalion had no choice but to attack.
Nos.10 and 11 Platoons of "T" Company advanced but came under heavy fire and were forced to take cover in some nearby buildings where a prolonged gunfight ensued. The only way for any progress to be made was for small groups of men to move through houses and back gardens; a painfully slow process as every building had to be checked for the enemy, and the tall fences between the gardens were difficult to climb and under constant enemy fire. Nevertheless, "T" Company dug their heels in and gradually edged their way forward. By dusk they had reached the point where the 3rd Battalion's "B" Company, now departed, had come to a halt in the morning, just a mile short of Arnhem Bridge. The attack, however, had cost the Battalion dearly, both in terms of time and lives; only twenty-two men from "T" Company were still on their feet.
With the 1st and 3rd Battalions losing strength and Sperrverband Spindler gaining it with every hour that passed, the outlook was not promising. At 20:00, however, hope arrived in the form of the fresh and intact 2nd South Staffords, with the 11th Battalion not far behind them. Both of these units had experienced difficulties with snipers and delaying actions in places where the 1st Battalion had earlier become stuck, however the paratroopers had cleared much of this opposition away and so their casualties had been negligible by comparison. The 11th Battalion had yet to arrive, but Lieutenant-Colonels Dobie and McCardie immediately held a meeting and discussed the possibility of a co-ordinated attack towards the Bridge.