Youth participation in sport is associated with positive developmental outcomes. The development of life skills is especially important for urban youth of color who are often underserved and face poor long-term outcomes. To service the needs of underserved youth, community youth sport programs have begun to utilize sport-based positive youth development (PYD). Through this approach, key adult figures such as sport program staff and parents/caregivers have been identified as important mechanisms for life skill development and the transfer of learning. The aim of the current study sought to better understand how key adult figures influence life skill outcomes of urban youth of color involved in a community sport-based PYD program. Hierarchical linear regression analyses were used to examine the independent and interactive effects of staff support and parent/caregiver support on youth life skill and transfer of learning outcomes. Results indicated that staff support and parent/caregiver support predicted youth life skill and transfer of learning outcomes, both independently and, in some cases, interactively.