The town of Štip is mentioned in the foundation inscription of the monastery of Lesnovo by the Serbian Despot Jovan Oliver in the year 1341(u štipě). The Serbian King Stefan Uroš IV Dušan donated several estates of Stefan Hralja Dragovol to the Monastery of Hilandar after 1343. Among them were 50 houses in Štip with all rights, bought property, vineyards, watermills and the marketplace (U gradu 50 kukьь...I trgь u Štipu/U gradu Štipu, u amboriju stasь paričkihь 50 sь všemi pravinami i kuplenicami, sь nivьjemь i vinogradi i vodenicami i těm’ge amboriju trьgь). The Serbian King Stefan Uroš IV Dušan confirmed in 1348, that the Monastery Hilandar was in possession of the Church of the Holy Archangel and 50 place with people, rights, watermills and vineyards in Štip (U Štipu crьkovь Arhangelь i u gradu 50 stasi sь ljudmi i sь pravinami i sь voděnicami i sь vinogradi). Emperor Stefan Dušan donated the town of Štip to the Monastery of Lesnovo (ѹ градѹ Щипѹ). Emperor Stefan Uroš IV Dušan gives the church of Saint John the Baptist (Sveti Ioan Krьstitelja) and several subjects, a Serb (Dragoslavь Srьblinь) an Albanian (Ginь Arbanasinь) and two Vlachs (Manoo Vlahь and Dragoslavь Vlahь) to the nobleman IVanko Probištitivoić. In the year 1381, the Serbian noblemen Konstantin Dragaš donated the town of Štip to the Monastery of Chilandar (И у граду Штипу).