The objective of this research was to analyse and understand the various factors which are driving the cloud adoption by the organisations for the Singapore market. Most of the Information technology vendors have changed their business model and evolved their product and services around cloud, hence it was interesting to analyse if the adoption is real and driven by the need stemming from the technology and business drivers. The current cloud ecosystems of the Singapore market were analysed to understand what the industry’s expectations were from the cloud service providers. The data of the cloud users from Singapore was collected and analysed using quantitative research methods with deductive approach using random sampling method. It was further tested for the hypothesis developed around links between cloud adoption and the size of the organisation, various other factors, industry verticals and COVID as a situation. The results proved that adoption is dependent on the technical and business drivers and the actual challenges and benefits were captured which could help cloud vendors incorporate those views to refine their offerings. The results further proved that there is significant correlation between the size of organisation and the cloud adoption by incorporating the sample from the bigger enterprises and further expanding this research for the other Southeast Asian nations could get a bigger and better view of the cloud market in the region as most of the corporate treat ASEAN as one single integrated market for their business planning.