In the past decades many cities and regions underwent structural transformations – e.g. in old industrialized ‘rust belts’ or in peripheral rural areas. Many of these shrinking cities have to face the challenges of long-term demographic and economic changes. While in the USA, shrinkage is often related to postindustrial transformations in other countries like Germany for example, the causes are related to changing demographics with declining birth rates and the effects of the German reunification. Many cities have tried to combat shrinkage and have thus developed a variety of policies and strategies like establishing substitute industries. To assess the sustainability of this approach this presentation shows the results of investigations regarding the cities Cleveland/USA and Bochum/Germany in a comparative analysis following the most similar/most different research design. The research shows new development paths for shrinking cities.