A key feature of government policy in the last 30 years is the use of sport programmes as a vehicle for social change aiming to benefit and improve the lives of marginalized and vulnerable members of society. Sports policy-makers and practitioners have sought to use the a??power of sporta?? through sport-based intervention programmes to tackle key social issues. The Homeless World Cup is an example of this, comprising a football tournament held annually since 2003 aiming to re-engage marginalized, vulnerable and socially excluded homeless people. This article focuses on a group of young male homeless players from a United Kingdom squad that attended the inaugural Homeless World Cup. Drawing upon observations and interview material, the findings centre on the benefits of engagement in the programme but also the challenges and difficulties specific to the circumstances surrounding this group of players. The article concludes with a preliminary assessment of the appropriateness of the HWC as a mechanism for assisting homeless people to overcome the multi-faceted and complex issues they face.