This article seeks to measure the development of law after transplanting common law and statutes from another country by conducting an empirical study of the citation of precedents and demography of disputes of insurance cases in Singapore. This article recognizes that there are justifications for Singapore to transplant English insurance law. However, this research shows that the transplantation of English commercial law into a small jurisdiction, even within the common law family, may cause the law to be in a static state if courts do not have enough cases to maintain the development of law or to consider new development in England. Copying English statutes completely would not solve most doctrinal problems when a large number of disputes are about contractual construction but doctrinal application. Instead of counting on courts to move the law forward, this article argues that legislative reform is necessary in the future to modernize Singapore’s insurance law. In light of recent developments in England, whether Singapore needs to transplant new UK statutes will be an issue that Singapore legislators might consider in the near future.