Immigrant associations known commonly as huiguan have long been a research area among specialists on the Overseas Chinese. Recently, the same subject has attracted increasing attention among scholars who attempt to examine urban life in late imperial China. In either case, the existing historical literature seems to have focused on the two following aspects of huiguan development: the various principles of organizational formation such as common native place, surname, occupation and the new locational identity, and how they interacted with one another and shaped the community structure; the functional relevance of huiguan firstly to the various needs of the immigrant society and the local elite, and secondly to the overriding concerns of the ruling authority, be it the Chinese imperial bureaucracy or the governing authorities in a foreign settlement. Yet few attempts have been made to delineate the longitudinal evolution of these associations over an extended period in any single locale, and above all, to provide an analytical framework to decipher the complex interplay of different forces behind organizational changes. Relying primarily on Chinese newspapers, huiguan archives and publications in Singapore,3 this paper represents a very preliminary effort along both lines. After a brief background discussion on the nineteenth century, I will try to document closely several significant features in the development of Chinese huiguan in Singapore between the turn of the century and the beginning of the Pacific War. The main thrust here is to demonstrate the possibility of going beyond number games, that pay too much attention to organizational inventory, to examine more substantive issues such as changes in organizational forms, the revamping of institutional set-ups, leadership turnover and varying functional priorities. Then the following section will seek to account for these organizational metamorphoses. It will be argued that our explanatory paradigm should at least consist of three categories of factors: domestic forces associated with community evolution; the impact of the host society; and influences emanating from China and particularly the native area.