Four-centuries-long encounters between the Ottoman Empire and the Grand Duchy of Muscovy/Russian Empire point to complex relations that have been triggered and defined mostly by territorial, trade disputes, and wars, and maintained by diplomatic rivalry and occasional military alliances. Starting as friendly encounters during Sultan Bayezid II reign at the beginning of the 16th century, these relations, essentially and persistently asymmetrical, reveal an initial and long Ottoman dominance over the Muscovy/Russian side; one that lasted from the early 16th to the late 18th century—whereby the two sides shared no direct borders, traded and did not fight each other until the late 17th century—followed by a late 18th-century and mid-19th-century Russian ascendency. This ascendency was achieved largely thanks to the military reform that Tsar/Emperor Peter the Great undertook, namely, the establishment of a standing and professional army and consequentially due to the many wars that Russia won throughout the 19th century; the decisive ones being those fought during the reign of Empress Catherine the Great. The mid-19th century and the early 20th century—which witnessed the implosion of the Russian Empire due to the Bolshevik Revolution and the break-up of the Ottoman Empire by Britain and France—was a long period that saw few and brief military alliances, contested trade relations and yet continued wars. It was ultimately marred by an Ottoman drive to counterbalance Russia’s dominance, while the latter sought to preserve it, by involving other European powers (British and French)—the most crucial moment being the British, French, and Ottoman armies defeating the Russian one in the Crimean War (1853–1856)—transforming their bilateral interactions into multilateral but unsustainable relations.