In the light of the global trends towards international assessment, inter-country comparison and policy convergence, this article critically discusses the contextual factors that influence educational success in Shanghai and Singapore. Focussing on the structural and cultural frames, this article maintains that the educational achievement in Shanghai and Singapore is due primarily to heavy governmental investment and intervention in education as evident in recent education reforms, coupled with the sociocultural values of a utilitarian and technocratic view of education and strong community support for academic excellence. This article further argues that the cultural frame has posed a challenge to the policymakers' vision to promote a more holistic, experiential and creative form of teaching and learning that goes beyond summative and written assessment. The case studies of Shanghai and Singapore illustrate the need for policymakers and educators to consider the impact of local conditions, values and constraints on educational outcomes.