The literature on postcolonialism covers a diverse set of geographic areas, cultures, timeframes, and economic and political circumstances. Within the context of this literature, this article focuses on two territories which underwent colonial transition right at the end of the twentieth century, and moved not to sovereignty but to reintegration with their motherland. Language in education systems has long been recognized not only as a very significant indicator of power relations in societies but also as a very important instrument for continuity and/or change. Hong Kong's education sector is a complex arena for language, in which English, Cantonese and Putonghua each play different and changing roles. Macao's education sector has all of these factors plus additional complexities arising from the place of Portuguese. The article notes various paradoxes in the ways that patterns developed in Hong Kong and Macao in the initial postcolonial period. It identifies lessons not only from comparison between Hong Kong and Macao, but also from comparison of experiences in the territories as a pair with experiences in other parts of the world. [Copyright of Comparative Education is the property of Routledge. Full article may be available at the publisher's website: http://dx.doi.org/10.1080/0305006042000231365]