Sport for development and peace (SDP) organizations aim to use sport as a means of fostering a range of positive societal outcomes, yet researchers have suggested that existing research and evaluative practices are troublesome with minimal reporting around mistakes and unintended negative outcomes. The purpose of this study was to explore the notion of failure in SDP from practitioners’ perspectives. Data were collected from 28 SDP leaders through semistructured interviews. The findings highlight how practitioners define failure in the context of SDP, their experiences of failure, and the lessons learned from those experiences. Furthermore, a set of strategies were identified for how SDP leaders can manage failure to stimulate learning and innovation, which can improve program outcomes and sustainability. The findings also have critical implications for funders and support agencies to transform existing funding systems and processes to be more receptive to the inherent uncertainty involved in SDP work.