Given Singapore's location at the confluence of important maritime trading routes, and that it was established as a British East India Company trading post in 1819, it is unsurprising that Singapore has become one of the centres of natural history collecting and research in Southeast Asia. Despite its small size, Singapore is home to a diverse herpetofauna assemblage and boasts a rich herpetological history. The first systematic studies of Singapore's herpetofauna (within the Linnaean binomial framework) date back to Stamford Raffles and the naturalists hired by him who first came to the island in 1819. Specimens that were collected during and after this time were deposited in museums worldwide. Over time, 39 species from Singapore were described as new to science. Due to the entrepôt nature of Singapore with its associated purchasing and trading of specimens (both alive and dead), poor record-keeping, and human introductions, numerous extraneous species from outside of Singapore were reported to occur on the island. Such issues have left a complicated legacy of ambiguous records and taxonomic complications concerning the identity of Singapore's species-rich herpetofauna, many of which were only resolved in the past 30-40 years. By compiling a comprehensive collection of records and publications relating to the herpetofauna of Singapore, we construct an updated and more accurate listing of the herpetofauna of Singapore. Our investigation culminated in the evaluation of 309 species, in which we compiled a final species checklist recognising 166 species (149 native and 17 non-native established species). Among the 149 native species are two caecilians, 24 frogs, one crocodilian, 13 turtles (three visitors), 34 lizards, and 75 snakes. Of the 17 non-native species are five frogs, four turtles, six lizards, and two snakes. The remaining 143 species represent species to be excluded from Singapore's herpetofauna species checklist. For each of the 309 species examined, we provide species accounts and explanatory annotations. Furthermore, we discuss Singapore's herpetofauna from a historical and conservation perspective. Immediate deforestation and nationwide urbanisation following colonisation completely eliminated many species from throughout much of the country and restricted them to small, degraded forest patches. We hope this publication highlights the importance of publishing observations and serves as a valuable resource to future researchers, naturalists, biological consultants, and policy makers in initiating studies on species ecology, distribution, status, and promoting conservation efforts to safeguard Singapore's herpetofauna.