During the 13th and 14th centuries, the city of Skopje, strategically placed in the valley of the river Vardar (Axios), along the route connecting the northern Balkans to the Aegean Sea, was contested by several empires of the time – Byzantine, Bulgarian, Serbian and Ottoman. Probably for that reason, historians who analyzed the information found in written sources about the city in that period have often been more interested in the macro-level of political events than in the micro-level of urban studies. The aim of the present paper is to illustrate how a rereading and reassessment of well-known and long since published Old Slavonic documents of Bulgarian and Serbian rulers from the 13th and 14th century opens new perspectives in historico-geographical research of the cityscape of Skopje and its surrounding area during a period of political changes in which it passed from the Byzantine Empire into the hands of the Serbian state ruled by King Stefan Uroš II Milutin.
