This study examines Cuba’s role in the two southern African countries of Angola and Namibia during the Cold War period. It argues that Cuba’s ideological motivations have been embodied in the mutually reinforcing concepts of proletarian internationalism and anti-imperialism. These conceptual perspectives constitute some of the central variables that influence Cuba’s foreign policy behaviour in international relations. It is within this context that one can understand Cuba’s involvement in Southern Africa. This study also attempts to explain that Cuban foreign policy towards Africa was based on two complementary and contextual objectives namely, promoting nationalism at home and nurturing revolutionary Marxist-Leninist governments, as well as supporting anti-colonial and anti-imperialist movements abroad. For the purpose of achieving these foreign policy objectives, Cuba not only engaged in state-to-state relations with Angola and Namibia; but had cordial relations with the rest of the continent and in particular Southern Africa, which also became a direct military testing ground for Cuba’s commitment to an anti-colonial and anti-imperialist revolutionary stance. Furthermore, the thesis shows that Cuba’s relentless hatred of imperialism is rooted in its historical relationship with the United States because from the turn of the century till 1958, the Americans interfered in Cuba’s internal affairs by supporting corrupt administrations and exploited the country. These practices by the United States laid the foundation for Cuba’s anti-colonialism and antiimperialism abroad. Ultimately, this thesis shows that Cuban involvement in Angola and Namibia can be conceptualised within these contexts (anti-imperialism, anti-colonialism, proletarian internationalism and revolutionary Marxism-Leninism). The role of Cuban nationalism in the realisation of these objectives and ideals, as well as its role in perpetuating and consolidating her foreign policy is assessed in this study. This nationalism and ideals of internationalism constitutes the central idea in the Cuban revolution. Finally, this thesis asserts that Cuban motives for getting involved in the politics of Southern Africa were not motivated by economic or imperialistic reasons. Rather, the historical similarity and colonial experiences between Africa and Cuba were some of the central causal factors.