Positive youth development (PYD) programs have significant health and well-being benefits, but these are rarely examined in low- or middle-income countries such as South Africa. LifeMatters is a 10-session PYD program combining elements of sport psychology and cognitive behavioural theory. We conducted a pragmatic trial of LifeMatters, implemented by trained university student facilitators with three groups of South African adolescents (n = 28; aged 13-19 years) in a low-resource setting. Paired t-tests and Wilcoxon signed-rank tests indicated improvements (pre- to post- program) in adolescent personal growth, self-efficacy, self-esteem, and PYD outcomes. Evaluation forms (qualitative data) revealed participants enjoyed the program content, connected with facilitators, learned psychological skills and prosocial values, had intentions to share learned content, and would repeat the program. Focus groups were performed with program facilitators and field notes documented implementation. Thematic analysis identified three themes relating to program content, -implementation, and -impact. Study feasibility was influenced by several overlapping challenges/barriers. LifeMatters was considered culturally relevant and effective; implementation outcomes, implications for practice, and suggested improvements are discussed. This pragmatic trial provides insight into the utility of using trained student facilitators to implement a PYD program teaching psychological skills to adolescents in a low-resource setting.