This article outlines a historical analysis of the development of Singapore’s education system during the period of 1920 to 1958, focusing on the historical, political, and social contexts that shaped education policies during this period. The study examines three significant stages of governance: the colonial era (1920–1942), the Japanese Occupation (1942–1945), and the pre-independence period (1946–1958). Using a qualitative historical research approach, this paper draws on archival materials, government reports, and secondary sources to analyze the ideologies and educational strategies employed by each regime to address Singapore’s education challenges. Key findings reveal that under colonial rule, education policies emphasized English-medium schools to support administrative needs, often neglecting local communities. The Japanese Occupation disrupted existing structures, introducing policies to promote Japanese language and culture, which were met with resistance. In the post-war pre-independence phase, efforts were made to expand access to education, standardize curricula, and address inequalities, laying the groundwork for a modern education system. The analysis underscores the profound influence of political ideologies and governance structures on educational priorities and outcomes. These insights demonstrate how Singapore’s early education policies evolved in response to shifting socio-political landscapes, contributing to the foundation of a system known today for its emphasis on equity and excellence. The paper highlights the importance of historical context in shaping education systems and suggests that lessons from Singapore’s past can inform contemporary education policy discussions, particularly in postcolonial and rapidly developing contexts.