In the 8th century, Arab-Moorish armies advanced into the north of the Iberian Peninsula, but as early as the 10th century the area was temporarily reconquered by the Christians (Reconquista). In the late 11th century, Count Pedro Ansúrez made the largely depopulated city his residence, expanded it, and promoted its repopulation (repoblación), which is why he is often considered the actual founder of the city. The University of Valladolid was founded in 1241 by Alfonso VIII of Castille. It is one of the oldest universities in the world.

In the 15th century, it became the capital of the Kingdom of Castile until Philip II moved the center of power to the newly built monastery residence Real Sitio de San Lorenzo de El Escorial near Madrid in 1561. In 1561 most of the city burned down but was rebuilt under Philip II.

The Convent of St. Paul was founded in 1276 by Violante of Aragon, daughter of Queen Violante of Hungary. At the same time, a collegiate church was built.

Between 1445 and 1468, Cardinal Juan de Torquemada, who had attended school in the monastery, commissioned a larger church to be built. His successors continued it until its completion in 1616.

The middle part of the facade was designed by Simón de Colonia († 1511) and is considered a masterpiece of the late Gothic Isabelline style.