Gender plays an important role in all facets of human life and although great strides have been made against the gender discrimination, still the progress is gradual and slow. More specifically, in the field of educational management and leadership women’s attempt to gain equal groundwork with men is quite evident but the former still face gender related barriers that hamper their progress. The current research focuses on investigating the role and perceptions of women principals in the field of educational management and leadership and on drawing comparisons between their role in upper secondary education in Greece and Sweden. Therefore, the investigation takes place in the municipality of Thessaloniki and Stockholm with female principals from upper secondary schools to take part in the study. Ten from each city respond to the questionnaire, which is specially designed in their native language. The present findings provide an insight about women’s motivation to become upper secondary school principals, the reasons for their under-representation, the variations in managerial qualities and styles as part of their feminine identity, the difficulties they face towards identifying a position and ways to augment their involvement in the field. Drawing on the evidence of the survey conducted in Thessaloniki, despite the great progress that has been achieved in Greece in the field of educational management and leadership in terms of gender, women are greatly under-represented in upper secondary school management positions and significantly face sociocultural constraints and discrimination in their career path. However, the results of the study in Stockholm disclose that women progressively possess the managerial field in education currently outnumbering their male superintendents.