This qualitative project explores the meanings young boys ascribe to sport experiences and how understandings and perspectives of sport differ between parent(s) and child. Thirteen five-year-old boys and their parent(s) (n = 17) took part in semi-structured interviews focusing on meanings associated with their sport and physical activity experiences. The boys undertook a drawing exercise as part of the interview to elicit their experiences as distinct from those of their parent(s). The seventeen parents were interviewed about their motivation for encouraging their sons to be active. The results indicated that the parents’ and boys’ constructions and understandings of the boys’ sport experienced differed in two important ways; the gendering of the sport experience, and the way in which the sport experience is conceptualized.