Pre-recorded presentation link: https://www.youtube.com/watch?v=EqzBsczEZGA The sociology of elite schooling has shown that elite boys’ schools can be a breeding ground for unhealthy masculinities that reproduce gendered inequality in a range of ways. Some research has shown that the culture in elite boys’ schools can be harmful for female teachers. Yet less is known about the women who are successful in occupying leadership positions in these schools and what their experiences may be able to tell us. This qualitative research investigates the perspectives of four former female leaders in elite boys’ schools concerning the gendered culture, with a view to enhancing knowledge about the obstacles aspiring women leaders may face in these schools, as well as the possible facilitators. This research is guided by a conceptual framework that examines gender and power in the context of elite boys’ schooling by bringing together three theorists. Joan Acker’s work on gendered organisations, Raewyn Connell’s hegemonic masculinity, and Judith Butler’s theory of a heterosexual matrix are combined as a lens to provide a richer insight into the experiences of these women. The first key finding of the research is that there are barriers for women in their pathway to leadership in elite boys’ schools from recruitment, through to promotion and this continues in leadership. The second is the way in which power is produced and how this power positions women. The final finding concerns the motivation for women in education more broadly and how this may inadvertently present a barrier in leadership. The research argues that elite boys’ schools in Australia are gendered organisations and through a production and reproduction of masculine privilege, women are disadvantaged. A hegemonic masculinity is cemented through a matrix of intelligibility by which certain performances of gender are expected. These performances present ‘truths’ which position women as subservient and presents barriers in the career paths of women in elite boys’ schools. Schools act as a microcosm of the community, reflecting and engaging with the greater political, social and economic issues and dynamics in society. As such, elite boys’ schools need to work toward more equal gendered power relations.