A global response to the rapid spread of the 2019 novel coronavirus disease (COVID-19) is imperative in order to reduce mortality and morbidity as well as preventing a country's health system from collapse. Singapore showed exceptional leadership in the containment of the spread of the virus, however through April 2020 the country experienced exponential growth in the number of infections, particularly migrant workers living in dormitories. The following historical case study provides an overview of Singapore's country profile, their healthcare system and the country's non pharmaceutical measures taken to mitigate and contain the spread of COVID-19 in the first few months of the pandemic. We explore the impact COVID-19 had on Singapore's economy at that time and the implications of the resultant social and political disruptions. We conclude our study by using mathematical modelling to explore confirmed COVID-19 cases in Singapore's local community and those living in dormitories and use this data to forecast the progression of the epidemic in Singapore given the non-pharmaceutical interventions in place at that time. Our results indicate the COVID-19 outbreak in Singapore increased 3-fold the initial doubling rate of 22.5 days in the first 2 months of the outbreak to 6.7 days in the 5th month; We note a faster doubling rate of 4.9 days for those living in dormitories compared to a doubling rate of 13.5 days for the rest of the community.