Women play a key role in educational leadership and management, yet they are under-represented in school headship positions in Ghana and across the globe. This study explored the socio-cultural and school-related factors responsible for women’s under-representation in senior high school headship positions in the Ahafo Region of Ghana.  It employed a case study design underpinned by the interpretivist paradigm and involved five (5) female heads of the schools selected through a homogeneous sampling technique. Data was collected through a semi-structured interview guide and analysed thematically. The study revealed that socio-cultural factors such as the non-involvement of women in decision-making in societies, marriage-related responsibilities, and gender discrimination affected women’s representation in headship positions negatively. It also emerged that school-related factors, including the preference by old students’ associations and appointing panels for male leaders, accounted for women’s under-representation in leadership positions in schools. The study concluded, among others, that negative perceptions of female leadership and discrimination against women in some communities affected their involvement in decision-making, a phenomenon linked to their under-representation in Senior High School headship positions. Therefore, the study recommended, among others, that various directorates of education in the region should collaborate with the leadership of Senior High Schools, such as the Conference of Heads of Assisted Secondary Schools, to organise programmes that raise awareness about gender discrimination and stereotypical tendencies in headship positions, and strategise to address such issues.