The Second World War had devastating effects on Città di Castello. The town underwent 11 bombing raids during the weeks preceding the liberation of the town from the German Army by the Allied Forces (22 July 1944) with the destruction of bridges, the railway station, waterworks, civil and industrial buildings. There was also heavy damage to the town gate of Porta Santa Maria's embattled tower. The Resistance movement against the German Army was made in this area by the "San Faustino" &" Pio Borri" Brigades in which many of the towns young people enlisted and after the towns Liberation, they joined the "Cremona" Brigade, continuing to aid the liberation towards the North and helping to free the town of Alfonsine.
Lieutenant-Colonel Venanzio Gabriotti, who had already gained Gold Medal for Military Valour during the First World War and was an important regional Politician and Bishop Carlo Liviero's close friend ( an important person during the time between the two wars), paid with his life in his fight for the freedom of the town when he was killed by the Nazis and Fascists on the shingle of the Scatorbia stream on 9th May 1944. One of the most heroic stands of the Umbrian Resistance.