Teachers’ reflection based on the analysis of their classroom practice is necessary for increasing practical ability to implement effective instruction. Regardless its widely accepted importance of systemic analysis of teachers’ classroom practice, it has been administered by superficial and conventional way that could not yield significant impact on teachers’ change. In order to facilitate meaningful practice related to the analysis of teachers’ classroom practice, appropriate support system should be developed. In this study, the researchers focused on the potential of web-based and video-based instructional analysis system that enable teachers and educators to engage in meaningful analytic as well as reflective activities. Based on the comparative analysis of the literature in the areas of analysis of classroom practice, video annotation tools, and computer assisted qualitative data analysis program, we could identify several important issues that should be considered for the future development of the web-based instructional analysis system. We suggest the system should be based on the web while supporting collaboration among participants, including diverse types of instructional evidence for analysis, and providing different analytic lens or framework. Additionally, we present several areas and functions that could be considered in the development process.