Teaching listening is one of the most difficult tasks for any EFL teachers. Listening is a complex process in which many things happen simultanously inside the mind. This study focuses on the challenges in teaching Senior Islamic high school in Yogyakarta. This research was conducted under descriptive qualitative research design. The study participants were senior Islamic high school private English teachers in Yogyakarta. The participants involved in this study were two teachers. The participants are deliberately chosen based on certain criteria. The first criterion for participants of this study is, must be an English teacher in elementary school in senior high school. The second impact is that participants have experience in teaching listening skills. The results of this study found 10 challenges in teaching listening skills. the challenges are Managing classes, coping with media technical problems, audio-visual subtitles with subtitles, making students aaware in pronunciation, catching up with speed of media, creating conducive environments, designing interesting classes, limited time, students 'lack vocabulary, teachers' difficulty to understand the material.