The charter, which is mentioning the settlement site Kalugerica, is a forged document for the Monastery of Chilandar attributed to King Stefan Uroš II Milutin. It summarises the possessions of Chilandar and confirms earlier donations amongst others in the town of Štip and its surroundings. The document was created in the years 1371 to 1378 during a legal dispute with the Monastery of St. Panteleimon on Mount Athos based on the existing charter of King Stefan Uroš IV Dušan from the 1330s. The charter is attesting a state of possessions of the Church of St. Archangel Michael in Štip, which was built by the Serbian nobleman Stefan Hrelja Dragovol, as they existed in the 1330s. The charter also attests the resettlement of abandoned settlements with people from foreign lands by the Serbian nobleman Hrelja (I selište Brěstokь prězь Luka na Běsnu Voděnicu i Kalugerica i Police pašište sь vsěmi pravinami i megjami sel těhь). The Byzantine Emperor Andronikos III Palaiologos in 1340/1341 confirmed the village Brěstokь as a property of the Hilandar Monastery. He states also the settlement site of Kalugerica in this context (πέραν τοῦ ἐκεῖσε ποταμοῦ, τερ ον ἀγρίδιον τὸ Μπροάστοτζιν, μέχρι τοῦ Ἀγρίου Νεροῦ καὶ τῆς Καλογραίας καὶ τοῦ Πολιτζοῦ). The Serbian King Stefan Uroš IV Dušan confirmed the donation of the village Kalugerica, a former land of Stefan Hrelja Dragovol, to the Monastery of Hilandar after May 1343 (selo Kalugerica/I po ōne strane rěke selo Brěstovica, do divije vode i do Kalugjerice i do Police). The village of Kalugerica is registered in the Defters for the Sanjak Köstendil in 1519 and from 1570 to 1573.