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This study examines the shifting patterns of transportation networks inside the Pearl River Delta (PRD) during the first half of 20th century. It first explores how the special legal status of British Hong Kong in the PRD shaped merchants’ business logistics. It explores why the concept of the triad of Canton-Hong Kong-Macau (Sheng-Gang-Ao) was introduced in the beginning of this century to emphasize the inter-dependence of these commercial competitors to maritime trade in South China. The changing shipping laws & introduction of the diesel powered steel ship which was much bigger and deep-water and fuel dependent than the sailboats, the leasehold of the New Territories of HK in 1899, the development of legal and illegal coolie trade and related commercial activities, the impact of the Sino-Japanese War and the Japanese occupation of Hong Kong and Canton from late 1930s to 1945, and the influence of the Chinese Civil War following WWII are focal points of discussions to the changing patterns of transportation webs among this emerging metropolitan. In the conclusion, as the result of the political, economic and technical factors, the dominance of Hong Kong in this region before the establishment of the People’s Republic of China in 1949 and the introduction of containership in 1955 is quantitatively analyzed. By employing the geographical information system (GIS) techniques, the study provides a firmer ground to evaluate the interactions of Canton, Hong Kong and Macau in the latter half of 20th century and giving evidences to forecast the future competitions and cooperation amongst different port cities of the PRD.