Professional tennis players have their own habits of tactics and play. However, players’ shortcomings can be corrected by constantly practicing professional techniques and by tactical analysis. Therefore, this study aimed to develop a two-stage, expert decision-making system for tennis matches. The first stage consisted in dividing the court area and defining the technical classification of the net. Tennis coaches were invited to assess tennis players’ skills on the competition court, dividing it into 48 areas on both sides of the court centerline and identifying the skills used by the players. In the second stage, a classification model was developed, and the score, hitting habits, and tennis skills of the players, Roger Federer and Rafael Nadal, over 10 matches, played from 2007 to 2019, were analyzed and classified using notational analysis and the C5.0 decision tree algorithm. The results show that the two players’ highest scored techniques were the forehand stroke in the backcourt and the backhand stroke in the half court. Thus, using this expert decision-making system, our data can provide other players with imaginary training objects from two of the top players in the world to be used during training and can allow the accumulation of experience for players through continuous simulation and training analysis.