Research has revealed that while pre-service teachers (PTs) with coaching orientations reinforce sexism and masculine bias, those with teaching orientations combat and reject it. The purpose of this study was to examine four sport education (SE) seasons taught by two experienced in-service teachers for the presence or absence of sexism and masculine bias. The concept of hegemonic masculinity (HM) served as the theoretical framework. A case study approach was employed. Data were collected through non-participant observations; formal, informal, and stimulated recall interviews; document analysis; and electronic journals. Analysis techniques used were analytic induction and constant comparison. Findings revealed that the in-service teachers were able to combat and reject the effects of HM to a greater extent than teaching-oriented pre-service teachers were shown to do in previous work. The foundations of the teachers’ effectiveness were their liberal beliefs about sport and gender, and the teaching orientations. In addition, the teachers were able to provide a relatively equitable experience for girls and smaller, less physically-able boys. This was because these teachers possessed good levels of curricular, pedagogical, content and pedagogical content knowledge, as well as superior knowledge of their pupils.