Because of its geographical location, halfway between Segovia and Valladolid, and the existence of the castle, the Villa played a role of some importance during the War of Independence, and the fortress a place coveted by the French.VELASCO BAYÓN, 1996, p. 521 As they did with other monuments in Cuéllar, such as the convents of San Francisco and La Trinidad or the church of San Pedro, the castle also fell victim to the theft and destruction of the French.VELASCO BAYÓN, 1996, p. 525 On 28 February 1808, the first French soldiers arrived, settled in the house of one of the noble families of Cuéllar and were fed and cared for by the population. Shortly afterwards, the Segovia Artillery Academy and General Gregorio García de la Cuesta from Valladolid took up arms against the French. The Duke's administrator, complying with orders from Segovia, sent all the firearms stored in the castle, for which four wagons were necessary.MONDÉJAR MANZANARES, 2007, p. 183
