This paper explores the possibilities and challenges of introducing gender history in the classroom. Whilst in recent years, history teachers have pushed for the inclusion of women’s history in the curriculum, very little has been written on gender history. Drawing on works by Olivey (2019,2022) and Benger (2020) on historical perspective, this paper considers how gender as an analytical lens for a historical period might be introduced in the classroom. It also considers what assumptions students have about gender roles in past societies, particularly surrounding the role of women. This case study centered around a four-lesson enquiry, focusing on the lives of two extraordinary women who challenged students’ initial assumptions about gender roles in the medieval period. This paper argues that students had deep misconceptions about medieval gender roles, and that for some, being introduced to these complex historical figures helped nuance their understanding of the medieval world.