This research proposes and tests a new taxi dispatch policy to improve the existing systems used by taxi companies in Singapore. The proposed method chains trips made by reservations at least 30 minutes before the customer pick-up times. In this paper, the taxi dispatching system, Singapore Taxi Advance Reservation (STAR), is defined. A novel trip-chaining strategy based on a customized algorithm of Pickup and Delivery Problem with Time Window (PDPTW) is proposed. The idea is to chain several taxi trips with demand time points that are spread out within a reasonable period of time and with each pick-up point in close proximity to the previous drop-off location. The strategy proposed has the potential to lower the taxi reservation fee in Singapore to encourage advance reservations that facilitate trip chaining, which translates to lower taxi fares for customers, higher revenue for taxi drivers, and lower fleet ownership cost for taxi companies.