[2] Although the locality was settled before, various research provided that the remaining walls were built in the late 14th century, during the rule of Prince Lazar of Serbia, as a defense from the Ottoman invasion.

During this time Serbia developed a sort of wine which was called Prokupac (from the grape of the same name), indicating that the city had a thriving wine-making industry.

Under Lazar Hrebeljanović and Stefan Lazarević, Prokuplje enjoyed the same status as Kruševac, Stalać, Bovan, Petrus, and Leskovac.

The fortress consists of a citadel with oval foundation, situated on the highest plateau, from where two concentric bulwarks descend forming two lower boroughs on accessible areas of the hillside.

The site on and around Hisar Hill is rich with valuable archeological findings from various eras; there were remains of Roman baths and fortifications, as well as pre-Roman and Byzantine foundations under sections of the lower town.