In this study, we look at the evolution of a cooperative water regime in the delta of the Rhine catchment. In a Dutch–German case study, we focus on cross-border cooperation on the local and regional scale, describing and analyzing how a remarkably resilient and robust transboundary water regime has evolved over the course of 50 years. Context-, interest- and knowledge-based explanations contribute important insights into the evolution of the Deltarhine regime, and it is shown that the legal, institutional and socio-economic context shapes and constrains regional cross-border cooperation. Surprisingly in this regard, we find that European water directives have not yet played a decisive, catalyzing role for policy harmonization across borders. Finally, we show that key individuals play a crucial role in regime formation and development. We suggest that the presence of entrepreneurs and leaders adds explanatory power to current conceptual frameworks in international river basin management, thus meriting further research.