Germany and the Netherlands have developed very differently over the centuries. A close examination of Dutch and German regions show the differentiated way in which regions profit from the changing developmental opportunities of the world-system. This article studies long-term regional development using regional urban population in the Netherlands and Northwest Germany. Initially the coastal regions profited from the emerging trade based agricultural world-system. Later on, state formation enabled some of the previously developed regions to regain their position. Industrialization concentrated the development. In recent times, development spreads, giving developmental opportunities to some previously disadvantaged regions that are well located and well-endowed to profit from the recent developments in the world-system.