At 04:30 hrs on 22nd October 1944 the artillery of XII Corps which consisted of six field regiments, two medium regiments and one heavy regiment Royal Artillery, over 200 guns, opened fire. They put down concentrations on all known German positions in preparation for the 53rd (Welsh) Division attack. At 06:30hrs the forward battalions begin their advance and the 53rd (Welsh) Division attack began.
The 71st Infantry Brigade, which was to the left of the Nijmegen — Den Bosch railway line astride the main road, advanced two battalions up with the 4th Battalion the Royal Welch Fusiliers and 1st Battalion the Highland Light Infantry left and right respectively. Opposing them were the two battalions of the 732 Grenadier Regiment and without any supporting armour their progress was slow.
The line of advance was heavily wooded and the Germans fought tenaciously all the way. Their axis of advance lay through Maleskamp and Vorkenshoek to Hintham. A Company 4th Battalion the Royal Welch Fusiliers lost all of their officers while clearing the large woods to the south of the road. At noon Brigadier Elrington committed his reserve battalion, the 1st Battalion the Oxfordshire and Buckinghamshire Light Infantry and they mopped up the enemy left in the wake of 1st Battalion the Highland Light Infantry north of the main road.
160th Infantry Brigade, who were to the right of 71st Infantry Brigade and north of the Nijmegen — Den Bosch railway line, advanced with the 4th Battalion the Welch Regiment and 2nd Battalion the Monmouthshire Regiment as their leading battalions. They were supported by the tanks of the 5th Inniskilling Dragoon Guards plus a number of Crocodiles and Flail tanks, and they made better progress.
The 2nd Battalion the Monmouthshire Regiment pioneers cleared the minefields supported by the tanks of the 5th Inniskilling Dragoon Guards, two of which were knocked out by German Sturmgeschütze [Stug] III self-propelled guns. Opposing them were the 745 Grenadier Regiment and the 2nd Battalion the Monmouthshire Regiment advanced some 3,000 yards capturing 255 prisoners and accounted for many more killed at a cost of just six casualties of their own. During the advance Sergeant William Niblett's platoon was held up by an enemy machine gun. He immediately took hold of a Bren gun and charged the enemy Spandau killing the three man crew . It was for actions of this kind that Sergeant William Niblett and Sergeant Leslie Davis, both of whom commanded platoons with dash and skill, were awarded the Military Medal. Private Ronald Warren single-handedly attacked and captured a four-man German mortar team and was also awarded the Military Medal. D Company 2nd Battalion the Monmouthshire Regiment reached Kruisstraat around 13:30 hrs.
The 4th Battalion the Welch Regiment advanced towards Nuland, which was some 1,500 yards from the start line and defended by 712 Fusilier Battalion. They advanced close behind the artillery barrage in order to prevent themselves from getting pinned down. Their assault was supported by Lieutenant Andrew Wilson's flame throwing Crocodile tanks that were capable of projecting a flame 100 yards and these flamed the village. The Major Lewis' A Company 4th Battalion the Welch Regiment followed close behind the flames and threw grenades into the enemy trenches before going in with their bayonets fixed.
By 07:45 hrs Nuland had been captured with a number of the enemy being taken prisoner. A group of 80 or so defended a burnt out factory along the main road and A Company 4th Battalion the Welch Regiment attacked supported by two tanks of 5th Inniskilling Dragoon Guards. They stormed the factory forcing the enemy out, those remaining adding to the growing number of prisoners of war. The commander of 745 Grenadier Regiment, Oberst Wust, and the commander of 712 Fusilier Battalion, Hauptmann Siebecker, were among those taken captive.
During the afternoon Major General Ross decided to reinforce the success of Brigade Coleman's 160th Infantry Brigade by pushing through the 1st Battalion the East Lancashire Regiment and 53rd Reconnaissance Regiment. At about 15:00 hrs, three hours later than intended, the long column of 111 vehicles began passing through the 2nd Battalion the Monmouthshire Regiment at Kruisstraat. This consisted of A Squadron 53rd Reconnaissance Regiment, B Squadron 5th Inniskilling Dragoon Guards, five Flail tanks, the 1st Battalion the East Lancashire Regiment in Kangaroos, 202 Field Ambulance, M10 tank destroyers, an anti-tank battery, AVREs and a number of Wasps, flame throwing universal carriers.
Soon after passing through 160th Infantry Brigade the leading recce car was hit and a Cromwell tank was blown up by a mine bring the long column to a grinding halt. D Company 1st Battalion the East Lancashire Regiment debussed from their Kangaroos and drove the enemy back whilst Flail tanks cleared a breach in the minefield. By now, however, it was dusk and the armoured thrust into 's-Hertogenbosch had failed and Major General Ross ordered 2nd Battalion the Monmouthshire Regiment to continue their advance.
The advance continued early on the 23rd when the 2nd Battalion the Monmouthshire Regiment passed through the 1st Battalion the East Lancashire Regiment towards Rosmalan. On the left 71st Infantry Brigade continued to work its way forward slowly and by the afternoon the 53rd (Welsh) Division was in a favourable position to assault 's-Hertogenbosch. Major General Ross issued orders for the assault that evening.