The republics that make up the South Caucasus today gained brief independence after the fall of the Tsarist Empire, before the integration of the region into Bolshevik Russia. This period, even though short, gives interesting historical background to understand the present. Thus, the purpose of this paper is to study the South Caucasian republics from 1918 to 1921 at the regional and international levels, paying particular attention to the historical continuities with the contemporary era (since 1991). The results of the study show three main parallels between the early twentieth century (1918–1921) and the present. First, the region is still internally divided (e.g. the unresolved conflicts). Second, externally, it is torn between sometimes opposing powers (e.g. Russia and the Western powers). Finally, third, the partnerships with international or regional powers still remain asymmetrical; consequently, the need to cooperate with Russia exceeds the aspirations of the Western powers toward the South Caucasus. Based on archival research, this study contributes to the historiography of the region and gives a framework for understanding the South Caucasus in contemporary international relations.