Singapore is one of the most industrialised and urbanised economies in South-East Asia. Power supply is an important sub-system in its economy and heavily reliant on imported oil and natural gas. Due to its geographical area, clean/renewable energy sources for power generation are limited. At the same time, in its deregulated electricity market, the adoption of clean/renewable based power generation technology may be hindered by a market pricing mechanism that does not reflect externality costs. For a sustainable power supply, there is a need to change the conventional appraisal techniques. Life cycle assessment (LCA) and life cycle cost analysis (LCCA) are good tools to quantify environmental impacts and economic implications. LCA and LCCA are performed for centralised and distributed power generation technologies in Singapore, namely, oil and Orimulsion-fired steam turbines, natural gas-fired combined cycle plant, solar PV and fuel cell systems. A life cycle energy, emission and cost inventory is established. The results are discussed from the perspectives of fuel security, environmental protection and cost effectiveness of future power generation strategies for Singapore.