While research into sport coach mentoring is steadily increasing, currently the literature base is overly mentee-centric, overlooking the role and importance of additional stakeholders (e.g. mentors, programme directors, and sport governing bodies) involved within formalised sport coach mentoring programmes. Consequently, the aim of this research was to address this issue by examining the experiences of Jason, a Programme Director (PD) of a high-performance formalised female sport coach mentoring programme. Data were collected via three in-depth semi-structured interviews, which were analysed thematically. The findings highlight the inherent complexities of planning and delivering effective formalised sport coach mentoring provision, especially within high-performance contexts. Challenges associated with mentor recruitment and training were outlined, alongside the external influences of organisational agendas and beliefs on mentor pedagogy and practice. Jason also critically reflected upon to the problematic nature of evaluating formalised sport coach mentoring programmes. Practical recommendations and future avenues for empirical inquiry are discussed.