This article critically examines some of the major challenges and dilemmas faced by sport-based intervention programs that aim to achieve social mobility of urban youth. Drawing on case studies from Brazil, Australia and The Netherlands, the author proposes and illustrates a typology for analysing sport-based social interventions, which incorporates the level and the focus of intervention. A number of barriers to successful intervention are identified, including persisting inequalities in sport participation, cultural expectations and norms, the competitive nature of sport, and the cost of sport engagement. It is argued that there are at least three major dilemmas in relation to using sport as a vehicle for social mobility of urban youth: balancing the intrinsic and extrinsic significance of sport ; the interrelationships between sport and other social fields ; and the demand for sustained and dialogical commitment by all parties involved, including funding bodies. It is concluded thatsport does not offer a panacea for social problems. Sport-based social intervention programs can make a difference for some people in some circumstances, depending on the ways in which these programs are delivered as well as on the specific conditions in which they operate.