The aim of this paper is to report data from a study that examined formalised mentoring as a learning strategy with professional sports coaches. Mentoring as a method of supporting and enhancing professional learning appears to be regarded by some sports organisations as something of a panacea that can resolve a range of learning problems. The study was framed by drawing on a cultural theory of learning which examines how individuals learn in different situations, and how learning cultures influence the practices, actions and dispositions of individuals. Data are reported from a twelve-month longitudinal study of four mentors and ten coach mentees in a UK national sports organisation. Findings from the study suggest that coaches’ and their mentors’ experiences of formalized mentoring were conditions of three dimensions: personal interplay, context (professional sport) and organisational culture. This clearly points to a theory of cultural learning which serves to recognise learning as a consequence of participants’ embodied engagement in mentoring practices, shaped by the culture in which such practices are situated. In conclusion, with stronger theoretical foundations in mentoring activities, the value to individuals, and professional sports organisations, of formalized mentoring as a way of supporting professional practice might be better realized.