The article considers the prerequisites and problems of the evolution of Russian-Ukrainian relations in the period from 2014 to 2022. Geopolitical causes of the reunification of Crimea with the Russian Federation in 2014, as well as the consequences of the mentioned event have been analyzed. The results of negotiations for settlement of the conflict in Ukraine within the framework of the Normandy format have been studied. It is emphasized that in the result of the failure to implement the Package of Measures for the Implementation of the Minsk Agreements the process of resolving the conflict in the South-East of Ukraine has reached a dead end. Moreover, the Ukrainian side, with the support of the states of the socalled collective West, has initiated the preparations to finish the conflict under consideration by military means. In addition, the transformation of the doctrinal documents that determined the Russian-Ukrainian relations has been analyzed. The active influence of the member states of the North Atlantic Treaty Organization on the foreign policy of Ukraine during the period under consideration is noted. The military and technical, reconnaissance, financial and diplomatic support provided to Ukraine by Western states, as well as the politics of Ukraine for implementation of the ideology of Ukrainian nationalism and Russophobia into society have been studied as the factors of transformation of Russian-Ukrainian relations, as well as the prerequisites for the Special Military Operation initiated by the Russian Federation on February 24, 2022.