The last few decades have provided multiple studies on gender, language and textbook materials in education. Textbooks often reflect our current social environment and after the revelation of gender stereotypes in them, they should be improved to better represent and reflect our society. However, there is still a need to investigate how textbooks represent social roles such as gender, to notice the transformation. Therefore, this study aims at researching two upper secondary textbooks in English to discover how gender issues are handled in them. The purpose of this comparative study is to unravel if, and if so in what ways, gender stereotypes are still prevalent in textbook materials to this day. Two textbooks were investigated through different themes to see how men and women were represented in them respectively. The primary materials that this study was based on were Blueprint B 3.0 and Solid Ground 2, the first published in 2018 and the latter in 2005. The method was based on content analysis and was developed with theme tables that were created to collect and examine data. The tables extracted for collection of data were, profession, physical attributes, socio-psychological features and discourse roles. From the results of these tables, a comparative analysis was then performed, in each section. Findings indicate that although women are being detached from what is traditionally associated with them, male representation in other than male dominated domains fails to acknowledge this aspect of gender equality. Hence, the representation of women and men in occupation, physical- and socio-psychological traits is still mediated in a stereotypical manner. The only result which did not present characters in a stereotypical manner was that of ascribed discourse role.