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The present paper explores the hitherto unknown beginnings of the Ottoman-Russian imperial rivalry by focusing on the mid-16th-century encounter between the Ottoman Empire and the Tsardom of Muscovy over the North Caucasus, where the ambitions of these two asymmetric powers--the Ottomans being an established "super power" and the Muscovites a rising power--became entangled for the first time. This first encounter, which was the harbinger of many future engagements not only in this region but also in the broader steppe frontier around the Black Sea, was more of a "cold war" rather than a military confrontation, as both the Ottomans and the Muscovites rather preferred to establish spheres of influence and eventually their hegemony over the North Caucasus through their vassals and clients. In addition to demonstrating the Tsardom of Muscovy's initial claims and policies over the North Caucasus, this study will shed light on the reasons of the Ottoman failure to transform their nominal claims over the region to a de facto hegemony similar to what they had established over Eastern European principalities. [ABSTRACT FROM AUTHOR]