This study aims to explore the educational structure through which out-of-school sport-based life skills education programs connect sport experiences to youth life skills learning and transfer, and to derive implications for their application in Korea. The cases selected for analysis were The First Tee, Girls on the Run, i9 Sports, and PeacePlayers, all of which aim to promote life skills development and positive youth development (PYD). Based on official program materials and relevant literature, this study conducted a comparative case study using literature analysis across five domains: educational goals, content structure, coach characteristics, operational methods, and educational influences. The findings show that the case programs commonly reconstructed sport not merely as physical activity or technical skill training, but as an educational medium for youth development. They also connected sport experiences to life skills learning and everyday life contexts through value-based educational goals, structured activity experiences, reflection and transfer, educational coaching, and community-based operation. However, the programs were not designed in a uniform way. Rather, they were organized around different developmental logics and transfer mechanisms, including self-management, social-emotional learning, behavioral norm formation, and community and citizenship development. Coaches also functioned not simply as technical instructors but as educational mediators who facilitated value learning, emotional support, behavioral feedback, and community relationship building according to each program’s goals. Program materials and previous studies reported changes and transfer possibilities related to self-management, confidence, relationship building, responsibility, leadership, and community awareness. These findings suggest that out-of-school sport-based life skills education is not a single fixed program model, but a youth development education model that can be implemented in diverse ways depending on its purpose and context. For the Korean context, the findings indicate the need to develop sport programs that combine life skills-centered curricula, transfer-facilitating structures, educational coaching systems, and community-based partnerships.