After the settlement of the Slavs, during the rule of Samuel, Radovis became an important merchant-craft and mining centre, while the medieval town of Konče was a monastery and episcopal centre. The town is mentioned for the first time in the year of 1019, in a Charter of the Byzantine emperor Vasilius 2nd, as a settlement and a regional town parish. At that time, the town was located in the North-West of the town's present location, on the banks of the Old river, where we can find traces of several churches, for example St. Archangel church.
Almost one millennium ago, Radovis queen (a princess of Slavic origin) Rada, was looking from the wall of the fortress (the old castle) when she became upset by her fiancee's exclamation Rado Vish (Rada look!). This exclamation that was supposed to warn her of the enemy attack, became according to the legend the name of the city, a synonym of its endurance over the centuries to come.
In the 14th century, after the destruction of the Byzantine Empire, Radovis found itself in the Serb medieval state. In 1361, the tsar Uros sojourned in Radovis. During the Ottoman Empire, at the beginning of the 16th century the area was settled by the Juruks - a Turkish nomad tribe, an ethnic group which in small numbers still inhabitates the region, while in the 17th Century under the Kjustendil sanjak, it belonged to the diocese of the Kjustendil metropolitan. At that time, the town had 3,000 - 4,000 inhabitants.
In the 19th and the 20th century, the town and its surroundings were influenced by the Razlovci (1876), Kresna (1878-1879) and Ilinden (1903) rebelions, later the events from the Balkan Wars (1912-1913), the First and Second World Wars.