This chapter traces the gravity of Russia-Sri Lanka relations from its infancy stage by examining the historical background, ideological rifts and cultural rifts that shaped the relations. Sri Lanka as a country located in a strategic point in the Indian Ocean is prone to external influences, which have played a cardinal role in the troubled history of the island nation. A proper study of Russia-Sri Lanka relations can unfold the early days of geopolitical foray in the Indian Ocean during the Cold War, in which Soviet Union too had its ambition in South Asian region along with the USA. However, the analysis emerging from this work argues that early policy of Soviet Union on Sri Lanka was a hostile one due to island nation’s affinity with the British, which resulted in opposition shown by Soviets when Sri Lanka applied for membership of the United Nations. This chapter further shows the changing dynamics of Russian-Sri Lankan relations after 1956 and its impacts upon Sri Lanka’s foreign policy. Also, this chapter argues that the bilateral relations between two states can be equated with Russia’s yearning for new global order under Putin as Sri Lanka falls within the Moscow’s novel strategy on the Global South. All in all, this chapter provides a comprehensive picture focusing on the imperative of Russia’s role in Sri Lankan foreign policy.