While sport for development programming has flourished, the complex social and economic environment in the postcolonial Eastern Caribbean is often overlooked by researchers. This case study examines sport for development with ‘at risk’ adolescent girls in St. Lucia (n = 16). These young women, who have been removed from mainstream public schools due to behavioural issues, participated in focus group discussions regarding their experiences and perspectives on sport. Their sport participation included single-sex, organised programming at the Upton Gardens Girls Centre and mixed-sex, unsupervised football play. Results of the study indicate that these sporting activities contributed towards the capability development of the participants, with limitations toward challenging gender stereotypes and encouraging kinetically focused body image. While the female-only sport participation encouraged a positive sense of self-efficacy and fostered peer/mentor relationships, engagement in co-educational football supported girls’ empowerment and the challenging of gender stereotypes. However, outcome towards progressive perspectives on sport and body image gleaned mixed results. As a whole, these results point to larger concerns within the sport for development field and the need for more in-depth and comprehensive critical research to better understand how sport impacts development initiatives.