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The origin of the Order of the Knights of S. Bento de Avis dates back to the Christian Reconquest, in the middle of the 12th century. Based in Évora, initially under the name of the Friars of Évora, after the city was conquered from the Moors. Under the aegis of the Spanish order of Calatrava, the knights were subsequently entitled the Militia of Évora or the Order of Calatrava. The knights then severed their ties with Spain and assumed the name of the Order of Avis when in 1211, D. Afonso II donated the town of Avis to the Friars, on condition that they would populate the settlement and build a castle there.

The first Master of the Order was Fernão de Anes (1196-1219), who oversaw the building of the town and castle. The last Master was Fernão Rodrigues de Sequeira, who died in 1433 and whose remains are buried inside the convent's church.

The Order’s most renowned figure was D. João, Master of Avis, the bastard son of D. Pedro I, who ascended to the throne of Portugal by popular demand after the interregnum of 1383-1385. The Order's name was thus linked to the Dynasty of Avis, the most notable of all Portugal's dynasties, which was responsible for the strategy that led to Portugal to opt for Atlantic expansion that culminated in the great Discoveries. From D. João I onwards, the order ceased to be governed by Masters elected by chapters of the order. From that time, its governors and administrators were chosen by the Crown. The first Master to be chosen under the new system was one of the King’s own sons. The king, D. Fernando, the "Saint", died as a martyr in Ceuta.

The Friars used a long, white cloak with cords that extended to their feet, and a green cross featuring a fleur-de-lis, the insignia of the Order.