Personalized, data-driven tactical analysis is crucial in modern tennis, yet automated systems that deliver player-specific tactical insights across matches remain scarce. We present a hybrid solution consisting of two complementary components: TennisTact and ChatTennis. TennisTact is an automated reporting system that continuously collects and processes extensive match data to deliver personalized tactical reports for tennis singles players. To overcome the rigidity of static reports, we pair TennisTact with ChatTennis, a multi-agent generative AI chatbot that draws on both shot-level and player-level databases to deliver on-demand, context-sensitive analyses. By combining the consistency and scalability of scheduled reporting with the flexibility of real-time dialogue, the system offers both commonly used player evaluation metrics and more customized evaluations while updating automatically after each day’s matches. This work bridges the gap between abundant online tennis data and actionable, player-specific tactical insights.