Organic farming makes up an increasing share of agricultural and food systems. Within organic agriculture, grasslands are of particular importance because of their multiple benefits to soils, crops, livestock and ecosystems. In this chapter, we review the multifunctionality of grasslands in the context of organic agriculture, with a special focus on crop rotations. Generally, differences between organic and non-organic systems are smaller for grasslands than for arable systems. However, marked differences between the production systems do occur with respect to nutrient management, particularly nitrogen. As nitrogen losses constitute one of the most important challenges for organic grassland management, we review current knowledge on the possibilities to contain such losses. Further we present two case studies, from the United Kingdom and Germany, showing that trade-offs between different aims, for example productivity and biodiversity conservation, are not restricted to conventionally managed grasslands but frequently occur in organic grassland systems as well.