During the year 2020, the world witnessed the reignition of an old conflict over the disputed land of Nagorno-Karabakh, between the countries of Armenia and Azerbaijan. Throughout the duration of conflict, curiosity arose with the different implementations of Enemy Images and how both countries used said enemy images. As both countries have their respective claims towards the land, either based on ethnic or historic facts, they did not shy away from pointing fingers at one another. Following the conflict, questions started formulating as to; how are the countries similar or different in the way they depict the “other’’; how are the countries visually depicting each other; how are they trying legitimize their actions; and how are two countries trying to depict themselves as the victim?Thus, a qualitative comparative case study analysis is implemented to help understand this phenomenon. Using readily available online data (i.e. new sources) allowed the researcher to compare the two countries and see how there is more to enemy images, and how they were used for legitimacy. The outcome of the study presented both similarities and differences between the two countries, and how they legitimize themselves towards the audience, through tools such as victimhood.