In Italy, the current reform of the planning system intends to modify the land-use planning model and to address regeneration and environmental issues in contemporary cities, involving both public and private actors. In this perspective, Performance-based planning can use market-based tools such as urban and territorial equalisation, compensation and local taxation to support and incentivise the design of Nature-based solutions, Green and blue infrastructures and Ecosystem services. This article presents research developed for the Metropolitan City of Milan. The research identifies a number of environmental indicators that evaluate the outcomes of the metropolitan and local planning process and actions. The evaluation will allow the Metropolitan City to differentiate financing policies and promote multiple actors to achieve sustainability goals using the territorial and urban equalisation tool and a connected bonus reward system.