This exploratory study examined the potential of using sport as a creative and engaging context to facilitate life skills development in socially vulnerable youth in Eswatini, who face major context-specific challenges to their healthy development. The sport for development program was designed using the Teaching Personal and Social Responsibility model with adaptations made to fit the cultural context. Participants in the program were local coaches (N=3 males) and socially vulnerable youth (N=48, 25 females and 23 males) aged 11-15 years old, recruited from a community-based organization. Coaches were trained as the primary implementers of the program. Data collection employed a mixed-methods approach that triangulated data from surveys, learning quizzes, focus groups, and interviews. Findings supported the potential value of the program in cultivating the development and possible transfer of personal responsibility (e.g., self-direction skills such as goal setting and decision making) and social responsibility (e.g., interpersonal skills such as respect, self-control, conflict resolution, and caring) behaviors. The study provided preliminary support for the contextual utility of engendering these developmental outcomes in an environment where youth are facing a major health threat (i.e., HIV/AIDS) and community challenges (e.g., gender-based violence, poverty). Continued investment in long-term sport for development programming in Eswatini is warranted.