Bilingual policy in Singapore has been characterized by dynamic government interventions since the nation’s independence in 1965. The elevation of English to the medium of instruction in education has inevitably come into conflict with Chinese, the lingua franca of Singapore’s dominant ethnic group. Drawing upon a theoretical perspective of prestige language planning, it is shown that the Chinese language has gradually lost prestige in Singaporean society in general, and in particular it has lost ground to English in terms of linguistic capital. A succinct re-examination of Singapore’s language-in-education planning shows that education alone cannot arrest the declining status of the Chinese language, neither does any image-fostering. The study highlights the importance of prestige promotion for the future success of Chinese language maintenance. The rapid rise of China provides an enabling environment for prestige manipulation. However, the socio-political goals of the Singaporean bilingual policy restrain the government’s willingness to support the unrestricted growth of Mandarin in the official discourse. Whilst this paper cannot provide solutions or suggest specific directions for solving this problem, it is hoped that the analysis of the complex interplay of the official discourse on language issues and the surrounding socio-political variables can shed some fresh light on understanding the intricacies and difficulties of a bilingual policy in a multicultural society.