Since the coming into force of the 1992 Republican Constitution of Ghana, women are being encouraged and empowered to take up leadership position and to take active part in decision making process like their male counterparts. However, women leaders are faced with many challenges in the performance of their responsibilities. This study, therefore, sought to find out the female leaders’ gendered perceptions and challenges facing them in educational leadership positions in the Sunyani West District of Ghana. The qualitative research approach was adopted using the case study design. The study was guided by these questions: (1) How do females in educational leadership positions perceive leaders?, and (2) What are the challenges facing women in school leadership positions? The study is delimited to perception of women in leadership and their challenges in educational setting in the Sunyani West District. Twenty participants comprising heads of senior high schools, departmental heads, senior housemistresses and female circuit supervisors were purposively sampled for the study. Interview and observation were employed for the data collection. Triangulation was employed to test the consistency of findings obtained through the different instruments used. The data was analysed through thematic approach. The findings of the study revealed that family factors and traditional male / female power relations constitute serious challenges to female educational leaders. Women in educational leadership positions are facing challenges due to roles conflict resulting from roles they play as mothers, wives, daughters and managers. Cultural beliefs and traditional perceptions on gender roles continue to serve as a barrier to women leaders. These challenges constitute social constraints that overshadow their leadership qualities. Negative self-judgement and its associated stereotypic conceptions of females in leadership dampen their competencies and make them feel inadequate. It therefore became evident that, there should be an urgent need to discourage the unfair, unjust and unequal treatment sometimes meted out on women when opportunity is given to them to become leaders. Women leaders should be encouraged by society to face and surmount these challenging realities in order to take their rightful place in leadership arena.