A tactically aware coach is key to improving tennis players’ games; a coach analyses past matches with two considerations in mind: 1) the style of the player and how that style translates to real-world shot-making, and 2) the intent of a shot, irrespective of the outcome. Modern Hawk-Eye technology deployed in top-tier tournaments has enabled deeper analysis of professional matches than ever before. The aim of this paper is to emulate and augment the qualities of great coaches using data collected by Hawk-Eye; we develop a deep learning approach to imitate tennis players’ responses, to learn individual player styles efficiently, and we demonstrate this using performance metrics and illustrations.