The article examines the role of the Cyprus issue in the bilateral relations between Greece and the USSR in 1956—1960. It is based on primal archival research realised at the Constantine Karamanlis Archive (AKK) and at the Diplomatic and Historical Archive of the Greek Foreign Ministry (DIAYE) in Athens. The analysis of the recently declassified documents relate to the events which took place in 1954, when the Soviet Union supported the Greek claims for self-determination of the Cypriot people in the United Nations on the basis of the anti-colonial principles. This contributed to the impressive increase in trade between Greece and the USSR, especially after the unofficial visit of the Soviet Foreign Minister D.T. Shepilov to Athens in 1956. Against the backdrop of the deterioration of the international situation in 1957, Kremlin heavily criticized NATO’s decision to deploy the US Intermediate Range Ballistic Missiles (IRBMs) in Europe and applied diplomatic pressures to NATO member-states including Greece. The shift from tensions to a peaceful offensive strategy, characteristic of the Soviet diplomacy towards Greece, proved to be a double-edged sword for Moscow in the long term. The author concludes that both countries exploited the Cyprus issue for their benefit. Thus, Moscow managed to take advantage of the Greek discontent with the NATO allies as a means of increasing its own prestige in the region, while the Greek governments capitalized on the Soviet tactics in order to increase its political leverage in confronting NATO on Cyprus. © Tasoulas A., 2021.