Women constitute a significant proportion of Malaysia’s teaching workforce and are increasingly represented in school leadership roles. However, their leadership experiences, constraints, and support mechanisms within Malaysian Independent Chinese Secondary Schools (MICSS), a culturally distinctive and community-governed school system, remain underexplored. Existing leadership research in Malaysia has largely focused on national schools, creating a contextual gap in understanding how gendered leadership unfolds within MICSS. This study aimed to investigate women leaders’ experiences and perceptions in MICSS, with particular attention to leadership challenges, adaptive strategies, and contributions to educational outcomes. Guided by Transformational Leadership Theory, Gender and Leadership Theory, Role Congruity Theory, and Glass Ceiling Theory, the study examined how cultural norms, organisational structures, and workload demands shape women’s leadership practices and professional experiences. A quantitative cross-sectional survey design was employed. Data were collected through structured questionnaires administered to school leaders, including principals, vice principals, senior assistants, and heads of department. The instrument measured leadership practices, perceived challenges, institutional support mechanisms, and leadership outcomes. Descriptive and inferential statistical analyses were conducted to identify patterns and relationships among key variables. The findings revealed that women leaders play a pivotal role in fostering positive school culture, strengthening teacher collaboration, promoting inclusive leadership practices, and supporting student development. Nevertheless, they continue to face substantial administrative workloads, work–life balance pressures, and structural constraints that limit leadership autonomy and advancement. Theoretically, this study extends gender and leadership scholarship by providing context-specific evidence from MICSS. Practically, it offers evidence-based insights to inform leadership development, mentoring, and policy initiatives aimed at strengthening women’s leadership effectiveness. The study also aligns with Sustainable Development Goal 4 (Quality Education) and Sustainable Development Goal 5 (Gender Equality) by highlighting the importance of inclusive and transformational school leadership.