According to the Life of Saint Prohor Pčinjski (11th century) Prohor settled in a small cave in the deserted area of Nagoričino in Žegligovo (vь Žegligovskoj straně). The Saint met the later Byzantine Emperor Romanos IV Diogenes (reigned 1068-1071), who was hunting in Žegligovo. Between 1300 and 1318/21 a certain anagnost Radin from Nagoričino in Žegligovo (anagnosta Radina Nagoričanina izь Žegligova) wrote a gospel for the priest Zagoranin in Sušica. According to the Lives of the Serbian Kings and Archbishops, written by Archbishop Danilo II and his successors, the Serbian King Stefan Uroš III Dečanski (reigned 1321-1331) gathered his army in the forefront of the Battle of Velbužd in the first half of 1330 on a field called Dobrič, located in today's South-Eastern Serbia at the confluence of the rivers Južna Morava and Toplica. He intended to confront the Bulgarian Tsar Michael III Šišman (reigned 1323-1330) at this place. As messengers informed him that the Bulgarian Tsar had reached the castle of Zemen in the upper course of the river Strymon (Struma), at that time the border between the Serbian Kingdom and the Second Bulgarian Empire, he set his army in march and first moved to Nagoričino, where he prayed in the Church of Saint George (priide vь monastirь svoi kь svetomu mučeniku Hristovu Georьgiju Nagoričьskomu). After the Serbian victory at the Battle of Velbužd near today's Kjustendil on 28 July 1330, Stefan Dečanski captured Michael Šišman and brought him to Žegligovo (aduxere eum in Segligovo), where he died and was buried in the Church of Saint George in the village of Nagoričino (et sepulchro datus est in Ecclesia sancti Georgii in pago Gorichina). In the year 1349 (u zemli žegligovьskoi) and 1354/55 respectively (u zemli žegligovьskoi) the Serbian Emperor Stefan Uroš IV Dušan (reigned 1331-1355) mentions Žegligovo in his charters for Church of the Presentation of the Holy Mother of God in the village of Arhiljevica. The localisation of Arhilevjica remains unsolved. It might have lain near Preševo (today in Serbia) or in the Skopska Crna Gora in the triangle of the villages of Belanovce, Domanovci and Izvorь. In the Serbian Annals a church in the Skopska Crna Gora above Žegligovo is mentioned (u Črьmьnyje Gory, vyše Žegligova; eius vero mater aedificavit Ecclesiam in Nigro Monte, supra Segligovo). The same source often conflates Žegligovo and Nagoričino in one unit (I u Nagoričinu na Žegligovo crьkov svetago velikomučenika Georgïa; i u Nagoričinu na Žegligovu crkovь svetago velikomučenika Georgïa; i u Nagoričinu na Žegligovu crkovь svetago mučenika Georgïa; i u Nagoričinu na Žegligovo crьkovь svetago velikomučenika Georgïa; i u Nagoričinu na Žegligovu crkovь svetago velikomučenika Georgïa). Žegligovo is mentioned by the Serbian Janissary Konstantin Mihailović (15th century) in his memoirs ("and as he [scilicet the Serbian Emperor Stefan Uroš V] reached the land of Constantine, he pitched his tent in the field of Žegligovo" and "as the Sultan Mehmed [II] arrived near the field called Žegligovo on the border of Rascia"). The term "Land of Constantine" relates to the Serbian Despot Konstantin Dragaš, who ruled over Žegligovo in the second half of the 14th century and was therefore called "Žegligovac". Žegligovo served probably as a deployment area for the Ottoman Sultan Murad I (reigned 1360-1389) before the Battle of Kosovo in June 1389 against the Serbian Prince Lazar Hrebeljanović (reigned 1373-1389). The Byzantine Short Chronicles report that the Ottoman Sultan Bāyezīd I (reigned 1389-1402) handed over the relics of Saint Hilarion of Moglena (11th/12th centuries) to Konstantin Dragaš in 1394, who resided in Žegligovo (ὁποῦ ἐκάθετον εἰς τὸν Ὀζίγλοβο). Thereupon, Konstantin brought the relics to the Monastery of Sarandaporь. In the year 1395 Konstantin Dragaš fell in the Battle of Rovine against the Wallachian Voivode Mircea the Elder (reigned 1386-1418). In the year 1479 the scribe Vladislav Gramatik compiled a liturgical book (Panegyrikon) in the Monastery of Saint Bogorodica Črьnogorska at the foot of the Črьna Gora (Skopska Crna Gora) in the region of Žegligovo (vь prědělě žegligovscěm). The humanist and diplomat Felix Petančić (ca. 1455-after 1517) refers to Žegligovo as "Gegligove". In 1512 Ottoman troops pillaged Žegligovo and Ovče Pole (To lěto plěniše Turci Žegligovo, Ovče Polě). In the summer of 1550 Klementios was appointed Metropolitan of Skopje, Vranje and Žegligovo (μητρόπολιν Σκοπίου, Βράνιας καὶ Ζεγληγόβου). Žegligovo is mentioned in the Vodičnički pomenik from the 16th century. The župa of Žegligovo roughly included the area to the South of Preševo (today in Serbia), to the West of Slavište, to the North of Ovče Pole and the valley of the river Vardar and to the East of the Skopska Crna Gora.