Technological pedagogical content knowledge (TPACK) has been well accepted as a framework to understand and describe types of knowledge required by teachers to teach specific content with technology effectively. However, limited studies have used the framework in analysing the complexity of technology integration in mathematics classrooms. This study investigates, through examining critical instructional events, the most influential TPACK constructs in understanding and shaping teachers’ pedagogical practices using digital technology. This case study was conducted in an early secondary mathematics classroom in Indonesia that used a web-based resource to support students’ understanding of fractions. The finding suggests that the qualitative examination of the four intersected TPACK constructs assists in understanding the challenges and the opportunities to teachers when utilising an exploratory-based technology. It demonstrates that the combination of pedagogical stances and choice of technology significantly influence the visibility of other TPACK constructs. Implications of this study include the need of thoughtful planning prior to using web-based resources and the importance to utilise critical events in developing and assessing teachers’ TPACK.