It is part of a large complex of buildings built in different historical periods, starting from the Muslim domination, and reaching completion as a fortress while a possession of the Order of Santiago.

The hill on which the monastery now stands was the site of a Celtiberian castro, a Bronze Age fortress used by the native Celts.

After Christians reconquered Uclés in 1174, King Alfonso VIII of Castile gave the fortress to the Order of Santiago, who made it their main headquarters.

After the end of the Reconquista, the buildings were remodeled, and many of the defensive elements of the fortress eliminated, giving it its current appearance.

Construction of the current monastery began on May 7, 1529, during the reign of Carlos V, Holy Roman Emperor, starting with the east wing, of Plateresque style.

In the 17th century, the work on the courtyard and the main staircase continued, and the west and south wings were finished.

Though plans existed in the early 20th century for the monastery to become a secondary school, and later a novitiate and college of Augustinians, it was ransacked and damaged in 1936 during the Spanish Civil War.

[3] Construction was carried out over a long period of time, so the monastery exhibits three architectural styles: Plateresque, Herrerian and Churrigueresque.

The rest of the monastery, built in the 17th century, is of Baroque style, and culminates with its Churrigueresque facade work by Pedro de Ribera.

The Plateresque decoration is clearly seen in the asymmetric windows of the eastern facade, in which skulls, shells, crosses, and other allegorical motifs are repeated.

The image of Carlos V, Holy Roman Emperor occupies the central place with its imperial attributes, a sword and an orb.

The painting of Saint James presiding the altarpiece is by Francisco Rizi, who was a portrait painter of Philip IV.

The decorative carvings include dolphins, lions, heads, warriors, trophies, fruits, and two crosses of Saint James.

At the bottom is the inscription Caput Ordinis ("Head of the Order"), freestanding crosses, a royal crown, knights with trophies, and chained Moors.