With the continuous decrease of the governmental funds in major public construction projects, expanding new overseas markets has become a business strategy considered by many Taiwanese contractors. Singapore is an overseas market possibly deserving for special consideration because of its favorable conditions, such as related location to Taiwan, stable political environment, and fair treatment to foreign contractors. To help Taiwanese contractors to bid for infrastructure projects in Singapore, this study analyzes Singapore's infrastructure procurement system and the procedure in applying for contractor licenses (work permits). Additionally, this work takes a construction project in Singapore, recently awarded to a Taiwanese construction company, as an example to illustrate the special features of Singapore infrastructure procurement system. The results reveal that a price-quality method for bid evaluations and a rigorous licensing process for assessing contactors' qualifications are the foundations of Singapore's procurement system. Moreover, several proactive mechanisms, such as request for information and submission of alternative offers, are also worth learning to improve Taiwan's procurement system.