Border cities have to cope with divergent interests more than other cities, because in the same place protection of national sovereignty clashes with local practices and international cross-border movements. The question of how economic, political, and societal transformations linked to the globalisation process shape the urban space of border towns should thus be answered through a multifaceted analysis. This article introduces the analytical framework of border intermediation, dealing with the internal characteristics of the city, its function in national and transnational networks, its relation to the direct rural environment and the ways in which the border conditions these dimensions. The two towns studied, Ouanaminthe and Dajabón, are located on the Haitian- Dominican border, which is strongly marked by its complex history since the times of French and Spanish colonization. This case study is based on qualitative methods — such as mapping use of urban space and interviewing local stakeholders and residents. Cartography and other primary and secondary sources complement these observations. Following the economic opening of the border, the remarkable demographic and spatial growth of both towns has dramatically changed ground property values. Urban development remained principally in the hands of landowners. Cross-border exchanges and the establishment of a “maquiladora” industry have had a different impact on the relations between both towns. At the local level, recognition of common problems has built some basic cross-border solidarity, supported by civil society and local governments. But this apprehension is not shared by the central governments and transnational economic actors, and it is undermined by strong prejudices of people on both sides. Both towns develop, following their own inherent characteristics, and despite the fact that they play common roles in cross-border networks, no bi-national urban space exists. The links between both towns are mainly functional and not strong enough for creating the sentiment of belonging together.