The article seeks to formulate a comparative framework that explains the uneven development of schooling in Cyprus and Singapore during the British colonial rule. It specifically focuses on the moment of transition to independence and on the role played by ideas and the interaction of ideas in the evolution of social institutions. The overall argument put forward is that the divergent ideational and institutional dynamics of schooling in the two settings at the moment of decolonisation were the outcome of the intersections of British colonial education policies, locally-indigenised cultural heritages, and relations with other nation-states in the region. These complex intersections permitted and, at the same time, constrained certain readings and re-readings of the continental European idea of mass schooling over time.