This paper considers gender differences in educational leadership theory and practice in two countries: Pakistan and United Kingdom. The differences are highlighted and explored through a comparative analysis of gender roles and its multitude effects on women. By undertaking the analysis, the research brings forth the different issues that are hampering the progress of women in educational leadership roles; the exacting demands of the developed world that still favor men over women and the societal frameworks in developing countries like Pakistan. The research repeatedly delves into the issue of differential treatment by including statistics and other insights to further inform the main hypothesis of the present research. The breadth of issues faced by women from both countries paint two stark but different realities. Moreover, the paper offers solutions in terms of what work needs to be done towards a more thoughtful understanding of leadership, in both countries.