The implementation of bilingual education has been a hot issue for public debate in Taiwan. Singapore’s experience of practicing bilingual education and being a highly successful country of internationalized its education system could be a good case for Taiwanese to study. This paper aims at providing an introduction to the historical context, developmental trajectory and the current achievements and challenges of bilingual education in Singapore from 1965 to present. Then, a contrast and discussion between the bilingual experience of Singapore and the policy agenda of bilingual education and bilingual nation in Taiwan are offered. This paper serves as a trigger for the readers to make a critical reflection on the Taiwanese policy agenda with the understanding of what happened in Singapore in the past 50 years.