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In this chapter we describe an innovative real-time fleet management system designed and implemented for eCourier Ltd (London, UK) for which patents are pending in the United States and elsewhere. This paper describes both the business challenges and benefits of the implementation of a real-time fleet management system (with reference to empirical metrics such as courier efficiency, service times, and financial data), as well as the theoretical and implementation challenges of constructing such a system. In short, the system dramatically reduces the requirements of human supervisors for fleet management, improves service and increases courier efficiency. We first illustrate the overall architecture, then depict the main algorithms, including the service territory zoning methodology, the travel time forecasting procedure and the job allocation heuristic