Cities face many challenges in their efforts to create more sustainable and resilient urban environments for their residents. Among these challenges is the structure of city administrations themselves. Partnerships between cities and universities are one way that cities can address some of the internal structural barriers to transformation. However, city–university partnerships do not necessarily generate transformative outcomes, and relationships between cities and universities are complicated by history, politics, and the structures the partnerships are attempting to overcome. In this paper, focus groups and trial evaluations from five city–university partnerships in three countries are used to develop a formative evaluation tool for city–university partnerships working on challenges of urban sustainability and resilience. The result is an evaluative tool that can be used in real-time by city–university partnerships in various stages of maturity to inform and improve collaborative efforts. The paper concludes with recommendations for creating partnerships between cities and universities capable of contributing to long-term sustainability transformations in cities.