The importance of the use of technology in mathematics education has been demonstrated by many studies. Effective use of technology has been found to support the conceptual understanding of students. However, it is also found that, having only technological knowledge is not sufficient for using technology effectively in teaching mathematics; technological knowledge must be supported by pedagogical and content knowledge as well. It is stated that a teacher who effectively integrates these three types of knowledge has technological pedagogical content knowledge (TPACK). In order for teachers to acquire this knowledge, it is important for them to take courses that support TPACK during their pre-service training. However, the type of instruction that they receive during such a course may have an impact on whether they actually acquire TPACK or not. In this study, we investigate a total of 80 pre-service teachers who took a class called “Exploring Geometry with Dynamic Geometry Applications” with different types of instruction over the course of 5 semesters. The participants involved a mixed group of junior, senior, and graduate students which allowed us to analyze the effect of class level and the type of instruction in the student’s ability to acquire TPACK. To analyze the students’ TPACK level, we performed document analysis using the theoretical framework developed by Bowers and Stephens after reinterpreting it based on the literature and the data collected during this study. It was found that the majority of the graduate students achieved Technological Content Knowledge (TCK). Additionally, it was observed that the type of instruction as well as students’ class level is important in developing TPACK. The obtained results allow us to make conclusions about how the contents and the instruction method of a course should be designed such that it better promotes TPACK achievement.