Given the key role coaches play in the experience of athletes, understanding the relationship between coach leadership styles and positive youth development (PYD) is crucial. This study examined the relationship of coach transformational leadership (TFL) to PYD. Athletes (n = 203) nested within 28 competitive youth basketball teams completed questionnaires about their coaches’ TFL, and two measures related to their own PYD – Youth Experiences for Sport, measuring PYD specific to the sport context, and a measure to assess the 5Cs (Competence, Confidence, Connection, Character, and Caring). Due to the nested nature of athletes within team and significant intraclass correlations, the predictive contribution of team and individual level perceptions of TFL was assessed with multilevel modeling. Individual and team perceptions of coach TFL significantly predicted 59% of the YES-S variance. In addition to team and individual main effects, a significant cross-level interaction predicted 20% of a player’s development of the 5Cs. Thus, athletes reporting above average coach TFL on teams reporting above average coach TFL reported the greatest 5C development. These results provide additional support for TFL as an avenue to foster PYD. Findings elucidate transformational coach behaviors that are related to positive experiences in youth sport and the 5Cs.