Saint Gavrilo Lesnovski came, according to the detailed Vita of him, from a rich family in Osečko pole (ōt strani Ōsečkōmъ pole, roditelemь bogatu sělo i blagočestivu). After a vision he built the Church of the Nativity of the Holy Mother of God with the funding of his parents on the field of Osiče (na pole Ōsiče). He then departed for the Lěsnovo Monastery (vь monastirь Lesnovskyj), from which he was released after a probationary period with the blessing of the abbot to enter a hermitage near the monastery and Zletovo (za nekoj skïtь blizь prjamo manastirь, vь dolь prjamo Zletovo). The lively influx of people, who were sick and obsessed, caused that the Saint sought solitude in Lukovo (i preide vo stranu Lukovo). The Saint Gavrilo Lesnovski escaped also from Lukovo and found refuge in the mountains, where he stayed on the mountain top Oblovъ until his death (verhъ Ōblovъ). The saint appeared in a dream to a Russian monk named Iosif and entrusted him to transfer his body from Oblovь to the Lěsnovo monastery. Iosif brought the relics of the Saint Gavrilo Lesnovski to the Monastery of Lěsnovo, where numerous miracles occured near the saints relics. In such a way the only daughter of a rich Armenian from Kratovo was healed (Vo gradь Kratovo). According to the Vita, the saint also came to the aid of a local Bulgarian prince named Mihail in the fight against the Pechenegs and Cumans. Mihail had to flee from his opponents to Ratkovica (vo stranu Ratkovicu). He was able with the assistance of the saint to sidle up to the opposing general Mavragan near Rataica in Zletovo (u Slětovo) and to kill him (u Rataicě i ubi Mavragana). Finally, the Vita also mentions the Serbian Despot Jovan Oliver and his erection of a large monastery church in Lěsnovo in honor of the saint, with which he replaced a small church building. The short life of the Saint Gavrilo Lesnovski, on the other hand, reports that the saint himself built the Lěsnovo monastery. The 12th-century Vita of the Saint Joakim Osogovski mentions the Church of the Saint Michael the Archangel in the mountains of Lěsnovo (Lesnovsuju gljemu goru...hram vь ime arhïstratiga Mihaila). The scribe Stanislavь completed in 1330 a Slavic manuscript in the Monastery of Saint Michael the Archangel in the mountains of Lěsnovo, which was in the domain of Ovče Pole and the region of Zletovo (vь ōblasti ōvčepolьskoi vь horě zljętovstěi, v gorě lěsnovьstěi, v monastiri stgo arhistratiga Mihaila). The scribe Stanislavь finished his prologue of the manuscript in the time, when Dragoslavь ruled over the land of Zletovo as Župan (ōbdrьžjaštu horoję Zlętovьskoję županu Dra’goslavu). In the course of the renovation of the monastery (1340/41) a Slavic donor inscription was placed on the stone at the katholikon. The inscription begins on a marble lintel above the entrance door in the west of the katholikon (i.e. on the eastern wall of the narthex), continues outside above the south entrance to the naos, can be dated to the year 1340/41 and mentions the katholikon as "Church of the Great Commander of Heavenly Hosts, Archangel Michael" (hramь velikago vojevode vy`snh silь arhistratiga mihaila). The grand duke (veliki vojvoda) Jovan Oliver with his wife Anna Mara and his son Kraiko, who were living during the reign of "King Stefan" (Stefan Uroš IV Dušan) are mentioned as the founders. According to the Slavic inscription, the following possessions belonged to the monastery at that time: the village near the monastery Lěsnovo, the hamlet Lukovo, the village Bakovo with the Church of Saint Nicholas (Sveti Nikola), the hamlet Globica, the village Dobrěevo, the Church of Holy Prophet Elisha (Sveti Elisei) in the village Drěvěno, the hamlet Peštno, the Church of the Saint Prokopios (Sveti Prokopie), the Katun of the Vlachs Stroi, the Church of Saint Nicholas (Sveti Nikola) of the priest Sïfie, twenty houses in the town of Štip and annually 100 perpers from the revenue of the market in Zletovo. The scribe Stanislavь copied a Menaion at the request of Jovan Oliver destined for the Monastery of the Saint Michael the Archangel in Lěsnovo in 1342 according to the colophon of the manuscript written in Slavic language (rukoju mnogogrěšnago Stanislava). The toponym Lěsnovo appears in this colophone (vь městě rekoměmь Лěsnově), although it is not clear whether this refers to the village or the monastery. Before the Serbian Emperor Stefan Uroš IV Dušan was able to found the bishopric of Zletovo with its seat in the Lěsnovo Monastery in 1346/47, he sought consensus with church and secular dignitaries. He reached the consensus with the Serbian Patriarch Joanikije II, the Archbishop Nikola of Ōhrid, the Metropolitan Jovan of Skopje and the founder of the monastery, the Serbian despot Jovan Oliver. In the founding charter of the Serbian Emperor Stefan Uroš IV. Dušan for the Eparchy of Zletovo with its seat in the Monastery Lěsnovo from the year 1346/47 the erection of the monastery by the Serbian Espot Jovan Oliver is mentioned (sьzdati jemu hramь vь ime velikoslavnyhь i besplьtnyihь činonačelnikьь arhistratiga Mihaila i Gabrïila, vь straně že zletovьscěi rekomōje Lěsnovo...v městě Lěsnově; crьkvi Arhanggelu u Zletovoi; podь crьkvь svetago Arhistratiga lěsnovьskoga). This plot of land gave its name to both the monastery and the neighboring village of Lěsnovo. A Greek inscription on a fresco above the entrance door in the west of the katholikon (i.e. on the eastern wall of the narthex) from 1349 shows that the narthex was erected and painted before 1349 (probably 1347/48) (ὁ θεῖος καὶ πάνσεπτος ναὸς τοῦ ταξιάρχου Μιχαὴλ). A note in the Slavic manuscript Lesnovski parenesis relates that it was written in Zletovo at the place called Lěsnovo in the Monastery of the Holy Archangel Michael in 1353 (vь zemli zljatovsьskoi, vь městě rekoměmь Lěsnovo, vь ōbiteli svetago arhistratiga Mihaila), as Arsenije was the Bishop of Zletovo. The Eparchy of Zletovo was probably abolished around 1370. The Serbian local ruler Konstantin Dragaš donated on the 15th August 1381 the Monastery Lěsnovo with all its possessions to the Hilandar Monastery (crьkvь lěsnovьsku svetagō Arhaaggela; crьkvь Svetagō arhaggela lěsnovьskoga). In 1428, 1429 and 1434 a Slavic Apostolos, a Slavic Mēnaion and a Slavic Oktōēchos were written in Lěsnovo, about which corresponding marginal notes provide information.