The aim of this study was to identify the impact of different tactical behaviors on the winning probability in table tennis. The performance analysis was done by mathematical simulation using a Markov chain model. 259 high-level table tennis games were evaluated by means of a new simulation approach using numerical derivation to remove the necessity to perform a second modeling step in order to determine the difficulty of tactical behaviors. Based on the derivation, several mathematical constructs like directional derivations and the gradient are examined for application in table tennis. Results reveal errors and long rallies as the most influencing game situations, together with the positive effect of risky play on the winning probability of losing players.