During the early Middle Ages there were very few data about the region of Takovo. The first evidences about the migration of the South Slav tribes who settled those lands were very poor.

At the end of the XIII century (1293) we already had the infallible data on Rudnik because then it belonged to King Dragutin as a part of "Srem Land".
Thanks to its remarkable economic significance the rulers of Nemanjic Dynasty, the Hungarians and other feudalists fought for Rudnik. During the Dynastic fights between King Stefan Uros II and his brother Dragutin, in 1302 Rudnik was in the possession of Uros, and in 1313 Dragutin ruled the city. Later, in 1323 and 1324 the Dynastic struggles were inflamed again, this time between Uros III and Vladislav. The most intensive fights were around Rudnik and Ostrvica.

In 1354 during the war between the Serbs and the Hungarians Tsar Dusan, himself stayed in this region. On August 14th in 1354, he signed a charter.
"On Brusnica at the foot of Rudnik mountain"
There were his seal and his signature on the charter.
"Honorable Stevan, Tsar of all Serbian and Greek lands, and of the sea coast and the Western sides."
That was the first time, known so far, that one of Takovo settlements was mentioned in the Medieval Times. During the war against Tsar Uros in 1359, the Hungarian king took Rudnik over temporarily and he drew out the charter.
After the death of Tsar Uros in 1371 during the fierce struggles among Serbian feudalists, Grand-Duke Lazar and Nikola Altomanovic fought for Rudnik.
When the Turks carried Novo Brdo (1441), Despot Djuradj Brankovic became particularly interested in Rudnik. He had his palaces and his courtiers there and there he often spent his summers. Djuradj Brankovic also had on his court Great Captain Radic Postupovic who owned, as a part of his patrimony, villages like Beluce (Crnuce), Vracevsnica, Rudnik itself, Prodanovci, Kamenica, Konjusa, and some other places. The man was also the founder of Vracevsnica Monastery, that the inscription in the south part of the Eastern wall of the vestibule of this monastery proves. At the end of this inscription you can read:
"......This Holy Temple of God was delineated, finished and ornamented by the Great Captain Radic in the name of Celebrated Great Martyr Saint George in the summer of 1431."
Besides Vracevsnica monastery, Postupovic also founded the monastery of Veliko Blagovestenje (The Great Annunciation monastery) on the river Grabovcica, village Grabovcica, that was first mentioned in 1429 and 1430. That monastery hasn't been preserved and the very place it was located, is not known.
Despot Djuradj Brankovic died in December in 1456 and he was buried in the church of the place Kriva Reka, in the upper course of the river that kept the name the Despotovica. His wife Jerina (known among the people as " Damned Jerina " ) died in Rudnik on May 3rd 1457.
On the basis of archival material kept in the archives in Dubrovnik and also on the basis of the archeological localities all around Rudnik we find out very significant facts about this big mining settlement.
The people of Dubrovnik and the Saxons had their powerful colonies on Rudnik even in XIV century. Except the people from Dubrovnik whose consul spent some time in Rudnik, there were also people from Split and Kotor. The trade spread to Venetian Republic, too and numerous Saxon colonies were called "The Saxon City".
On the left bank of the river Jasenica, the catholic church, called "Misa" was built because of the presence of a great number of Catholic Religion inhabitants. When they took Rudnik over, the Turks turned this church into the mosque, too, like many others. The ruins of "Misa" ( or the mosque) can be easily noticed even now. Even more traces from the Middle Ages remained around Jezero, Cesmica, the Majdan river. On the mountains to the northwest towards the Jasenica river, there are still many substructures of the old buildings. We should distinguish "The Cities" among them all.

Medieval Serbian rulers coined their own money in Rudnik, but Rudnik with its mineral riches was not the only source of income of Serbian rulers. It was the place where the handicrafts were developed, where the trade bloomed; it was a cosmopolitan city in small, from where the cultural influence was spread to whole Serbia.

Except Rudnik and Ostrvica where the traces of Medieval culture have been best preserved, in a couple of villages you can still find so called "Greek" and "Hungarian" cemeteries. The best preserved "Greek graveyard" is on Lipa in Majdan with its 200 tombstones and that represents one of the oldest necropolis in this area.