Traumatic exposure can lead to negative outcomes for youth such as difficulties with attention, damaged sense of self, and disengagement, which can be exhibited in various ways (e.g., inability to handle pressure or loss, aggression, difficulties in regulating emotions). Leaders trained in trauma-informed practices can design and deliver sport programming that minimizes the occurrence of these negative outcomes, by providing youth opportunities for socialization, skill development, and engagement. To date, little research has explored experiences in the design and delivery of a trauma-informed sport program. In collaboration with a national non-profit community organisation that targets at-risk youth, the pilot year of a trauma-informed sport program was developed and implemented. Fifteen leaders from three different sites across Canada participated in two multi-day trainings on trauma-informed practices and then implemented a yearlong BBL program at their respective clubhouses. This was a mixed-methods study in which data were collected from the leaders via individual interviews, focus groups, logbooks, surveys, and archives of an online community of practice. These sources were analyzed using deductive-inductive thematic analysis. Three major themes were identified concerning successes (e.g., gains in leaders' confidence, knowledge, and adherence to approach use), challenges (e.g., recruitment of youth, time limitations, social-behavioural issues of youth), and future goals (e.g., enhancing marketing strategies, consistency in staffing, suggestions for training improvement, adopting roles). This evaluation has led to informed modifications for the second year of this trauma-informed sport program and has several practical implications for researchers and practitioners involved in developing and implementing trauma-informed sport programming.