Diversification of cropping systems has been proposed as a major mechanism to move towards sustainable cropping systems. To date, a diversification option that has received little attention is introduction of ley pastures into cropping systems, but the use of ley pastures is challenged by most future-oriented scenarios aiming to feed the world sustainably. In these scenarios, ruminant livestock feed only on permanent pastures, while cropping systems focus completely on production of crop-based human food. Diversification of cropping systems with ley pastures is thus compromised by knowledge gaps and future-oriented policy options. Here, we review ecosystem services provided by introducing ley pastures into cropping systems to increase sustainability of agriculture, discuss types of ley pastures and their management liable to promote these services, and raise future challenges related to introducing ley pastures into cropping systems. We conclude that (1) ley pastures provide a large set of input (soil conservation, nutrient provision and recycling, soil water retention, biological control of pests) and output (water purification, climate regulation, habitat provision for biodiversity conservation, forage production) ecosystem services of primary importance to cropping systems and society, respectively, as long as their spatial and temporal insertion within cropping systems is well-managed; otherwise, disservices may be produced. (2) To benefit from ecosystem services provided by ley pastures in cropping systems while limiting their disservices, it appears necessary to define a safe operating space for ley pastures in cropping systems. Moving towards this space requires changing plant breeding programs towards multiservice ley pastures, producing knowledge about emerging ways of introducing ley pastures into cropping systems (e.g., living mulch, green manure) and better quantifying the bundles of ecosystem services provided by ley pastures in cropping systems.