This article reviews how Singapore has responded to the COVID-19 pandemic, from late-January to early May, 2020, through the three-phase approach to “learning”: in-between learning, trial-and-error learning, and contingency learning. Given its unique political system dominated by the People’s Action Party (PAP) and bureaucratic culture, the Singapore government has progressively implemented numerous control measures including strict travel bans, contact tracing, “Circuit Breaker,” compulsory mask-wearing, and social distancing policies, along with financial relief to businesses and workers, in a very top-down fashion. Although the health and treatment issues of foreign migrant workers in dormitories continue to be the subject of ongoing debate among many scholars, it should be noted that the mortality rate in Singapore still remains very low compared to that of many other countries. Singapore’s case points to an important lesson that learning-driven coordinated strategic approaches matter for effective crisis management in the long term.