The mouthpiece geometry of single-reed instruments has been known to have a great impact on sound quality and playability. Although many researchers have investigated the effects of the geometry using artificial blowing machines or user case studies, few attention has been paid to the essential cause of physical changes in the instrument. In this study, we propose a method combining the artificial blowing machine and numerical flow simulations to explore the player’s feelings about the airflow and sound generation in the clarinet mouthpiece. With the artificial blowing machine, the mouth pressure, as well as lip force, were systematically changed using a pressure regulator and strain gauge. At particular conditions, the numerical flow simulation was conducted by solving fluid–structure interactions with the Navier–Stokes equations and the one-dimensional beam equation. The playability of the mouthpiece was shown by the changes in oscillation threshold pressures and sound spectral characteristics, whereas the cause of the changes could be described by the airflow pressures inside the mouthpieces. The results suggest that the combination of the artificial blower and the flow simulations can be effectively used for clarifying the cause of changes in players’ feelings.