Germany and the Netherlands have developed very differently over the centuries. A closeexamination of Dutch and German regions show the differentiated way in which regions profitfrom the changing developmental opportunities of the world-system. This article studies long-term regional development using regional urban population in the Netherlands and NorthwestGermany. 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 regaintheir position. Industrialization concentrated the development. In recent times, developmentspreads, giving developmental opportunities to some previously disadvantaged regions that arewell located and well-endowed to profit from the recent developments in the world-system.