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Business environment in which a port carries out its operation is increasingly reflected by intra- and inter-port competition on regional and global scales, resulting in port concentration and deconcentration. While a number of recent studies interpret those phenomena as impacts from global forces such as containerisation, little has been done about local forces such as the evolving relationships between urban policy and port growth. This paper proposes to compare how the two global hub port cities of Hong Kong and Singapore have sustained their port activities while transforming into major economic centres. Entropy indexes are calculated by district, based on service industries related to port activities between 1993 and 2004. Results show the spatial shifts of port-related activities stemming from simultaneous factors, such as port competition which affects the international position of Hong Kong and Singapore, and lack of space and congestion at the port-city interface. However, one main differentiating factor in the evolution of the two hub port cities is the varying impact of regional cross-border relations with mainland China and Malaysia