The article is devoted to so called “Macedonian issue” that emerged in the 19th century, its historical and political development and influence on modern international relations between the two countries - Bulgaria and North Macedonia. The authors consider the problem in the international and regional contexts. Particular attention is paid to the prospects for the development of negotiation processes between Bulgaria and North Macedonia in connection with the resolution of unresolved pressing historical issues from ancient times, entailing a number of problems, including blocking the entry of North Macedonia into the European Union and calling it an equal member of the European community. © 2021, Rossiiskaya Akademiya Nauk, Institut Istorii (Russian Academy of Sciences, Institute of General Hist. All rights reserved.