In recent years, Russia and Turkey have been among non-Western powers that have been more assertive in their foreign policies in the Western Balkans. Naturally, this creates the need to identify the key similarities and differences between these two geopolitical players. By using the case of Serbia, the pivotal country of the Western Balkans and a country whose foreign policy was largely influenced by the idea of hedging and engaging non-Western players, one can determine key similarities and differences between these two powers. This paper states two major similarities between these two powers and one major difference. The first similarity is that both Russia and Turkey are acting based on the same permissive environment of a regional power vacuum, the environment in which the EU’s leverage has decreased and in which countries like Serbia feel emboldened to hedge their bets and diversify partnerships. The second similarity is that although the popular explanation is to stress to powers’ ethnic and religious ties with the Balkans, Slavic and Orthodox ties in case of Russia and Islam in case of Turkey, or even as the continuation of old imperial traditions, the two countries are guided by strategic pragmatism. The difference between the two powers is that Russia can be defined as a status quo power as it aims to act as a spoiler perpetuating the current state of political dysfunctions; Turkey is not a status quo player as it does not oppose the region’s membership in Western institutions as long as its interests are respected.