This study aimed to investigate the effects of two different racket models and two different forehand drive velocities on the three-dimensional vibration behavior of the racket and shock transmission to the player’s wrist under real playing conditions. Nine tennis players performed a series of crosscourt flat forehand drives at two velocities, using a lightly and a highly vibrant racket. Two accelerometers were fixed on the racket frame and the player’s wrist. The analysis of vibration signals in both time and frequency domains showed no interaction effect of velocity and racket conditions either on the racket vibration behavior or on shock transmission. An increase in playing velocity enlarged the amount of vibrations at the racket and wrist, but weakly altered their frequency content. As compared to a racket perceived as highly vibrating, a racket perceived as lightly vibrating damped longer in the out-of-plane axis of the racket and shorter on the other axis of the racket and on the wrist, and displayed a lower amount of energy in the high frequency of the vibration signal at the racket and wrist. These findings indicated that the playing velocity must be controlled when investigating the vibration loads due to the racket under real playing conditions. Similarly, a reduced perception of vibration by the tennis player would be linked to decreased amplitude of the racket vibration signal, which may concentrate the signal energy in the low frequencies.