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This study explores the representation of women in higher education leadership, and the factors that enable or hinder women’s progression and sustained presence in leadership positions. The persistent underrepresentation of women in higher education leadership and the associated forms of inequality are examined through the glass-ceiling which is widely recognized in research. To gain further insight into how gender disparity unfolds in Turkish higher education context, a sequential explanatory mixed-methods study has been conducted to analyze the gender distribution in leadership across 52 universities between 1993 and 2024, and examine the enablers and barriers affecting women’s progression and sustainable presence. Adopting Amartya Sen’s Capability Approach, this study aims to contribute to the ongoing endeavor to achieve gender parity in leadership.