While Sint-Oedenrode welcomed the Allies jubilantly on 17 September 1944, neighbouring Olland still sighed under the yoke of the occupying forces. The Germans' headquarters were located in Olland's parsonage. Artillery and machine guns are set up in several places in Olland. Olland finds itself in the front line of the Allies and the Germans for weeks. In early October, residents are told to leave the village. Those who dare to return will be shot. It is a sad exodus of large families, often with very young children, who have to leave hearth and home behind. Accompanied by German soldiers with rifles, a long line of people leaves the village in the direction of Boxtel. Many are taken in by relatives and acquaintances in Kasteren, Boxtel, Gemonde and Sint-Michielsgestel. Wednesday 4 October 1944 is a particularly gloomy day for Olland. There is a change of troops on the German side, a parachute battalion under Major Jungwirth takes over Olland and the surrounding area. As a precaution, the tower of the Roman Catholic church is blown up. But the rest is also totally destroyed, possibly hit by British shells. This is followed by more than two weeks of artillery exchanges with much destruction of houses and loss of livestock.

On 23 October, Operation Colin begins. The 51st Highland Division liberates Schijndel and Olland. In the early morning of 23 October, one unit, the 5th Battalion Seaforth Highlanders, sets off along the Ollandseweg towards Olland. Without any losses, they manage to capture Olland. They suffer only from mines and trees as road blocks. By evening they set up their command post at the Slophoos, near the so-called ‘German railwayline’.

After Boxtel was also liberated on 25 October, most of the evacuees return. Some stay a little longer at their hiding addresses. The scene that confronts the returnees is heart rending. Olland appears to have been hit hard. Much is in ruins, house after house burnt down or destroyed, craters in the road. Many cattle have been killed by shells. The church has been totally destroyed. It is a picture typical of the liberation in many Brabant towns and villages. But thanks to the evacuation, there were only few civilian casualties.