Programme evaluation has developed tremendously over the past 50 years, with a proliferation of evaluation research, an increase in the institutionalization of evaluation, and growth in the professionalization of evaluation. However, existing research and developments are still largely in North America, Europe, Australia, and New Zealand, with less from Asia. As theory building of policy and programme evaluation practices necessarily occur within specific political, economic, and cultural contexts, the applicability of Western-centric evaluation literature in Asian contexts warrants further examination. In this article, we explore the interconnections between evaluation theory, evaluation policy, and evaluation practice in the Ministry of Education Headquarters (MOE-HQ) in Singapore. We describe our theory of change of how evaluation theory influenced evaluation practice from the ground-up at the micro (individual) level, and from the top-down at the meso (organization) level. In the process, we also discuss how common challenges and tensions in evaluation (e.g., evaluation as an accountability vis-à-vis learning tool; appropriateness of randomized controlled trials vis-à-vis other approaches) acted out and were mitigated. We conclude with our learning points and implications for future research.