The healthcare sector is growing rapidly and taking up a significant portion of the GDP in developed countries. The healthcare industry faces significant challenges such as ballooning costs, shortage of qualified personnel, rapidly aging population, and increase of chronic and epidemic diseases. Information technology (IT) has been suggested as a mitigator for some of these challenges. Particularly, IT can enable automation, management, and integration of clinical and business operations for greater efficiency and effectiveness. Studying the evolution of IT in healthcare is essential to be able to understand the past trends, address the current situation, move to the nest stage, and make use of IT to advance the future. However, although there is considerable literature on IT evolution, we observe a lack of studies specific to the evolution of healthcare IT. With the unique challenges of this sector, we attempt to address this gap in this paper. This study will start with a literature review on IT evolution and then develop a model for the evolution of healthcare IT based on the Nolan stage model and its subsequent refinements. The model will be developed with an initial focus on healthcare IT in Singapore. The reason for choosing Singapore is because of its advanced IT and medical infrastructure, yet the spending on healthcare is relatively low compared to other developed countries. In future, our model will be extended to other developed countries in the Asia-Pacific region e.g., Australia and New Zealand, as well as the UK and US.