This chapter will discuss the history and evolution of European Metropolitan Regions in Germany, giving particular attention to top-down and bottom-up influences in shaping the regions of today. Using two examples of metropolitan regions, one monocentric (Berlin/Brandenburg) and one polycentric (Rhine-Ruhr), the challenges of regional cooperation and metropolitan institution-building are discussed. The chapter concludes with a discussion of the experiences with metropolitan governance and spatial planning in Germany to date, and the potential future challenges of regional cooperation in this complex multi-level system. In comparison to other European countries, Germany was late in setting out a nation-wide policy framework for ‘European Metropolitan Regions.’ The emphasis on metropolitan regions to strengthen the national competitiveness has created tensions with the long-standing objective of equality of living conditions. To date, 11 European Metropolitan Regions have been designated, which together cover more than half of the German territory. The differences between the metropolitan regions, in terms of size, spatial structure or population density, are significant, and different paths have been followed in bringing the metropolitan region concept to life and setting up metropolitan governance arrangements.