The Bulgarian Khan Boris built in the 9th century churches in Ovče Pole according to a Bulgarian chronicle (i na rěcě Brěgalnici, i tu prïemь carьstvo; na Ovči poli sьzda běli crьkvi). The Vita of Saint Prohor Pčinjski (11th century) gives account about Prohor, who came from a village in Ovče Pole (ōt vesї ovčopolskija). The disarmed Pechenegs were, according to Ioannes Skylitzes, settled on the plains of Ovče Pole in the first half of the 11th century (ἀνά τε τὰς πεδιάδας τῆς Σαρδικῆς, τῆς Ναϊσσοῦ καὶ τῆς Εὐτζαπόλεως διασπείρας πάντας καὶ πᾶν ὅπλον ἀφελόμενος διὰ τὸ ἀνεπιβούλευτον). The Nicene Empire conquered in 1246 parts of Macedonia, including Ovče Pole (Νευστάπολίς). Nine years later, in 1255, the Byzantine Emperor Theodoros II. Laskaris led his army through the Ovče Pole (διὰ τῆς Νευσταπόλεως), which was a waterless and houseless area (ἄνυδρος δέ ἐστιν ὁ τόπος καὶ ἄοικος καὶ πλήθει στρατευμάτων δυσβάδιστος). Ephraim (ἅμ’ Εὐτζαπόλει, resp. διὰ Ναυτζαπόλεως ἀνύδρου τόπου) and also Theodoros Skutariotes (Νευστάπολίς, resp. διὰ τῆς Νευσταπόλεως) describe both conquests. Ovče Pole (Ovьče Polje) was incorporated in the Serbian dominion under the Serbian King Stefan Uroš II Milutin in 1282/83. A poem in honor of the Byzantine general Michael Dukas Glabas Tarchaneiotes, which is the work of the Byzantine writer Manuel Philes (13th/14th c.), mentions amongst others the Byzantine conquest of Ovče Pole (Εὐτζάπολιν δὲ συλλαβὼν Μοροβίσδου, Σκόπιά τε Σθλάβιτζαν ἐξ εὐανδρίας, Καὶ τὸν Πίαντζον καὶ τὸ περὶ τὸν Στρόμον, Καὶ τὸν περὶ Στρούμμιτζαν ἄφθονον τόπον). The region (strana) of Ovče Pole (i Ōvčepolsku) is attested in the interpolated charter of the Serbian King Stefan Uroš II Milutin for the Hilandar Monastery from the year 1303/1304 (or after 1331?). The byzantine-serbian border in Macedonia became the central subject of negotiations in 1308 between the Serbian King Stefan Uroš II Milutin and Charles de Valois, when the latter sought to conquer the Byzantine Empire. The area of Ovče Pole (et contrata Ouciepoullie) should remain according to the treaty in the Serbian kingdom. The Serbian annals give account about the miraculous epiphany of the Saint Nicholas to the Serbian King Stefan Uroš III Dečanski in the Church of Saint Nicholas in Ovče Pole, where the saint healed the blindness of the king (et cum fuisset in Ovczepolye, in templo S. Nicolai). The same miracle is attested in the Vita of Stefan Dečanski, which was written by Grigorij Camblak (15th century; polje ovčee imenuemo). In 1330 the scribe Stanislav finished a Slavonic manuscript in the domain of Ovče Pole in the region of Zletovo on the mountains of Lěsnovo in the Monastery of Saint Archangel Michael (vь ōblasti ōvčepolьskoi vь horě zletovstěi, vь gorě lěsnovьstěi, vь monastiri stgo arhistratiga Mihaila). The same notice in the manuscript mentions that the Serbian King Stefan Uroš III Dečanski took control over Ovče Pole (i ōvčepolьsko). In the charter of Stefan Dečanski for the Monastery of Saint Nikola Mrački (Pešterski manastir) from the year 1330 appears the term zemli Ovčepolьskoi. From the slavic colophon of the scribe Stanislav in the Menaion of the Serbian Despot Jovan Oliver for the Monastery of the Saint Archangel Michael in Lesnovo from the 1342 results, that Jovan Oliver ruled at that time over the entire area of Ovče Pole (ōblastiju vseju ōvčepolьskoju). The Serbian Emperor mentions Ovče Pole (na Ovči Poli) in his charter for the Monastery of the Saint Archangels Michael and Gabriel near Prizren. The monks of the Hilandar Monastery complained in 1355 to the Serbian Emperor Stefan Uroš IV Dušan about the border violations by the people, who lived in the villages, which belonged to Karьba (selě zem'li Kar'bin'čkoi), whereupon the governor (kefalija) of Štip named David Mihojević (poslach kjefaliju Štip'skoga Davida Michojevikja) was sent out to determine the boundaries of the monastery in this area. In the boundary description of the Hilandar Monastery near the land of Karьba also Ovče Pole is mentioned (po ōnoi straně odь Ovča Polja). The Serbian Emperor Stefan Uroš IV Dušan issued on the 2th Mai 1355 the charter for the Hilandar Monastery in Ovče Pole (na Ovči Poli). The Serbian Emperor Stefan Uroš IV Dušan confirmed on the 17th Mai 1355 at the state council (sabor) in Krupište the tenure of the Monastery of Saint Petar Koriški as metochion for the Hilandar Monastery. The charters in question were written by the Serbian Logothet Gjurg in Ovče Pole (na Ovči Poli, resp. na Ovči Polii). The Serbian Emperor Stefan Uroš IV Dušan issued on the 2th July at the state council in Krupište the third charter for the Hilandar Monastery, which was again written by the same Serbian Logothet in Ovče Pole (na Ovči Poli). In the forged charter from the 15th century, previously referred as a document issued by the Serbian King Stefan Uroš II Milutin for the settlement Ulijare around 1318, amongst other places also Ovče Pole is mentioned (Ōvče polje). The Serbian Despot Stefan Lazarević granted in 1408/1409 a safe conduct to the ottoman troops from the area of Toplica via Kosovo to Ovče Pole (prohode kь Ovčju polju). In spring and summer of 1413 the two Ottoman pretenders to the throne Mehmed and Musa fought for supremacy on the Balkan Peninsula. Mehmed was supported by the Serbian Despot Stefan Lazarević. In the course of the military operations, Musa initially stayed in the Ovče Pole (in the Ragusan sources called Ovcepogle). Then Mehmed and Stefan Lazarević together with their troops crossed the Črьna Gora (Prěšьdьše že Črьmnu Goru) and reached the Ovče Pole (kь Ovьčju polju), where Djuradj Branković, Stefan's nephew, took command over the Serbian contingents. The Ottoman troops plundered the region of Žegligovo and Ovče Pole in 1512 (to lěto plěniše Turci Žegligovo, Ovče Polě). Ovče Pole is registered in the Defters for the Sanjak Köstendil between the years 1570 and 1572 as a summer pasture. Ovče Pole (Ovče polje is mentioned in the Pomenik from 15th–18th century. The Serbian scribe and copyist Jerotej Račanin travelled through the Ovče Pole on his pilgrimage to the Holy Land in 1704. He describes the area of Ovče Pole as beautiful, rich in fields, grain, vineyards and all kinds of fruit, with beautiful rivers and cold, pure sources, with cities and villages.