The healthcare industry faces significant challenges such as spiraling costs, shortage of qualified personnel, a rapidly aging population, and increase in chronic diseases as well as epidemics. Healthcare information technology (IT) has been suggested as a mitigator for some of these challenges. Particularly, IT can enable the automation, integration, and management of clinical and administrative functions in healthcare. This has the potential to lower costs, relieve the workload of healthcare professionals, and obtain improvements in healthcare quality as advances in IT take place. In this regard, studying the stages of healthcare IT progression is essential to understand the past trends, address the current challenges, and make use of IT to enhance the provision of healthcare in future. However, although there is considerable literature on the stages of IT evolution, studies specific to healthcare IT are sparse. With the unique challenges of the healthcare sector, we aim to address such a gap in our study. Drawing on the Nolan stage model, we propose a model to explain the stages of IT evolution in the healthcare sector, incorporating initiation, contagion, control, and integration stages. The model was developed with a focus on healthcare IT in Singapore, due to Singapore's advanced IT and medical infrastructure and relatively lower spending on healthcare compared to other developed countries. In this manner, this study contributes to the understanding of the role of IT in healthcare from a dynamic and evolutionary view.