Zimbabwe has always been striving to achieve gender equality since gaining political independence in 1980. But still, few women hold the position of primary school head. This study was designed to identify and describe factors behind the persistent underrepresentation of women in primary school headship in Masvingo province. The study indicated that women teachers did not enter into school headship roles due to low self esteem and lack of support from their families and the education system. Others tended to give preference to their domestic roles on the expense of their own career advancement and as a result, some of them did not apply when advertisements for school headship came out. The respondents suggested that perhaps the affirmative action policies together with the empowerment of women could assist in increasing the number of women entering school headship positions.