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Social inclusion is broadly recognized as a priority to accomplish at an international level. While the influence of sport toward this social mission has been largely debated, literature lacks contributions capturing the challenges of sport when promoting social inclusion. Based in case study methodology, the investigation explores the impact of a multi-stakeholder sport initiative developing social inclusion for socially vulnerable youth and the related challenges of the intervention through in-depth interviews with diverse program stakeholders. The main findings indicated the emergence of four challenges: limited transferability of program outcomes for youth in living conditions of severe vulnerability; drop-out of youth in living conditions of severe vulnerability; limited sustainability of program social workers; lack of sports club management skills. The work highlights some limits of sport-based programs for social inclusion and discusses some implications for practice to maximize the societal impact of such interventions.