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The loss of significant Byzantine and post-Byzantine documents from the archives of the Monastery deprives us of the ability to understand the history of the Monastery during the following Byzantine centuries in sufficient depth. Surviving documents provide us with sporadic information, such as the conquest of the Monastery in 1285 by pirates and the subsequent slaughter of many monks, while in 1307, the Monastery was looted by Catalan mercenaries.
However, around the 14th century, the Monastery was put under royal protection, and is characterised in documents from this period as the ‘venerable royal monastery’. During this period, important construction projects were carried out.

Until 1078, conditions at the Monastery experienced a gradual decline without, however, ever being abandoned, as was the case for many other monasteries.
The starting point for the improvement of conditions was the arrival in 1078 of Stefanos, an important Byzantine official from Vigla, for the purpose of embracing the monastic life. Stefanos, who came from a well-known Athenian family and had a large fortune, had been assigned to the Monastery by the Proto of Mt Athos, made a large monetary contribution for the conservation of the Protaton church, and along with three followers, took up residence at the Monastery. He was soon tonsured as a monk, taking the name Symeon and at the same time receiving the designation ‘Blessed’, and became Abbot of the Monastery. Symeon initiated important reconstruction work at the Monastery, which was virtually in ruins, an event which earned him the title of its new owner.

The Holy Xenofon provided for the construction of a medium-sized monastery complex, and wrote a Testament or Typiko (Book of Rules), which regulated different issues of the operation and communal life of the fathers in the Monastery. After Xenofon resigned as Abbot in 1018, the leadership of the Monastery was assumed by his brother Theodoros, who directed the Monastery at least until 1035. That year was the first time the Monastery is mentioned, obviously after.

The oldest historical proofs for the existence of the Monastery come from two documents from the Vatopedinos Monastery which are dated 998 and 1001, and are signed by the first owner, the Holy Xenofon, as ‘monk and Abbot of the Monastery of St Georgios’. The Holy Xenofon, who is mentioned also in the Life of St Athanasios the Athonite, was highly educated, which is evidenced by documents he both authored and wrote in his own hand, and his active participation in different issues involving the Athonite monasteries, as witnessed by his signature on relevant documents as late as 1017, the year the last one is dated to. The Monastery took its name from this holy monk, as is strongly supported by the monk Iakovos Neasketiotis in his 19th century work Αθωνιάς (‘Athos’).

A long-standing, respected tradition of the Monastery, based on evidence in its art and the composition of its hymns, connects its founding with St Xenofon the Senator in the 6th century A.D., and in particular with the construction of a small chapel dedicated to St Dimitrios, surrounded by a number of buildings. This tradition places the founding of the Monastery in the period before that of the Holy Athonite (St Athanasios) – the obscure phase of Athonite monasticism – which in some cases has been confirmed by evidence from recent archaeological excavations.