The basic structure and rhetoric of national language policy in multilingual Singapore has stayed essentially unaltered since independence with four official languages positioned within the national quadrilingual framework and employed in all public spheres, and individual bilingualism fostered in the private sphere. However, also since independence, there has been an active undercurrent of contradictions, proposing that the seeming top–down, undisputed language policy is in fact an active contested space, especially in how these policies are executed in schools. Specifically, this study is interested in language shift, maintenance and medium of instruction policies, their consistencies and disconnections. To grasp the apparent tension between static quadrilingual language policy and planning and the dynamic reality of policy shifts, this paper assumes Bourdieu’s metaphor of field. In so doing, it takes analyses beyond a Fishmanian domain-based framework (Fishman in La Linguist 1(2):67–88, 1965) which frequently informs language policy assay in Singapore but miscarries to capture fully the paradoxical shifts and affects that different fields have on each other regarding language and the power dynamics involved (Savage and Silva in Cult Sociol 7(2):111–126, 2013. doi: 10.1177/1749975512473992). It refers to Chinese and Indian language varieties as primary examples, displaying how a field assay exposes the various evolutions and paradoxes in policies for these languages.