Listening is highly critical as it is the first skill that is acquired from birth. However, this skill can be developed if it is acquired through proper methods and approaches. The purpose of this study is to identify whether technology-assisted context-based teaching improves the listening skills of teacher candidates. The research was based on a mixed research approach where quantitative data were obtained through experimental study and qualitative data were obtained through interviews. The study group of the research consisted of 50 teacher candidates in total; - 25 in the experimental group and 25 in the control group - who took the Comprehension Techniques II: Listening Education course in the Turkish Language Teaching department of Near East University in Northern Cyprus during the 2016-2017 academic year. The topics were conveyed to the experimental group using a context-based approach with technology-assisted context-based teaching, meaning the digital stories and drama method. A traditional method and approach was applied to the control group. “Listening Success Tests” and “Student interview forms” developed by the researchers were used for data collection. The obtained quantitative data were analysed using the Mann-Whitney U test, while qualitative data were analysed through content analysis. As a result of the findings obtained in the listening success tests, it was seen that there was a significant difference between the experimental group on which technology-assisted context-based teaching was applied and the control group where traditional teaching was used. Thus, it was proved that this approach applied to the experimental group was highly beneficial for developing the listening skills of the teacher candidates. Additionally, based on the opinions of the teacher candidates, it was revealed that this approach improved the listening skills from several perspectives.