English in Singapore has always presented a balancing act for its founders. The colonial era saw a distinct role for English, i.e. to produce English-speaking officers for the British administration, while modern Singapore sees English being used as both a national and international lingua franca and as a major language that connects the island city-state to the world. ‘English-knowing bilingualism’ has gained ascendancy in Singapore and may become a core competency for the 21st-century world with the rise in status of English as a global language. However, the path to English-knowing bilingualism in the pluri-lingual and heterogeneous country was often marked by paradoxical debates surrounding the issues of language maintenance and shift, identity and the transmission of values, equity and meritocracy, as well as balancing between local versus global linguistic norms and standards. This paper focuses on the continuing debates, from the past to the present, as new challenges arise and argues how a new balance has to be achieved in the language strategy, policy and management for future-readiness in Singapore.