During the Middle Ages, at the site of today's Casa Tencalla, there was a castle. The castle is first mentioned in 1054. On the mountain side surrounded by fortified walls, were the entrance gates to the village. Bissone was the center of the Ghibellines' resistance during the dispute between Milan and Como (1118–27). Following the French invasion in 1798 and the end of the Old Swiss Confederacy, it became a stronghold of supporters of the Cisalpine Republic. However, on 3 March 1798 it was taken over by Pro-Swiss forces from Lugano.