This paper dissects and compares the British colonial venture in Nigeria, India, Pakistan, and Malaysia, and their historical journeys toward federalism. It explores whether these postcolonial federations align with Stepan’s categories of the genesis of federations. Expanding on Stepan’s contribution, the concept of postcolonial federalism develops a new lens to scrutinize the complex relationship between colonialism and federalism, especially for its proposed cases, highlighting their unique structuring through colonial socio-political engineering. Moreover, it argues that the creation of these federations was carried out to facilitate colonial administration with complete disregard for the existing linguistic, ethnic, cultural, and religious cleavages leaving federalization as the only alternative to gain sovereignty. Finally, this paper discusses the scope of postcolonial federalism and its unique characteristics compared to Stepan’s typology on the genesis of federations. This paper acts as a safeguard against the notion of the federal arrangement only being a product of democratic, liberal, and contractual phenomena. At the same time, the concept of postcolonial federalism offers a new lens to conduct further research on federalism in the Global South.