This chapter explores historical and contemporary perspectives on women’s roles in leadership in education, tracking their journey from marginalisation to greater involvement and influence. Although significant progress has been made towards achieving gender equity in educational leadership, challenges remain, underscoring the need for ongoing efforts to promote inclusivity and empowerment. Adopting a Systematic Literature Review (SLR) approach, the chapter consolidates findings from the literature to provide a comprehensive understanding of the challenges and successes of women’s leadership in education. The research adheres to the PRISMA (Preferred Reporting Items for Systematic Reviews and Meta-Analyses) guidelines to ensure methodological rigour and clarity. It focuses on empirical, peer-reviewed studies published between 2014 and 2024, sourced from reputable databases such as Scopus, Web of Science, ERIC, and Google Scholar. Of an initial selection of 1100 articles, 28 met the inclusion criteria and underwent thematic analysis to identify recurring themes, challenges, and transformative strategies. The findings highlight both systemic obstacles and significant achievements in women’s leadership roles, influenced by reforms and advocacy. Ongoing issues, such as stereotyping and inadequate professional development, coexist with the opportunities made possible by mentorship and gender-sensitive policies. The strategies and successes of women leaders highlight the necessity for tailored, context-specific solutions. The study advocates for targeted interventions and policy reforms to create a more equitable and inclusive environment for women in educational leadership. These findings provide essential insights for advancing gender equity on an international scale.