The raceway damage of the bearing restricts the operation stability of the system. Therefore, in the case of damage, simulating vibration response and predicting the performance of the shaft-cylindrical roller-bearing-pedestal system have high research value. According to the structural characteristics and the force transfer relationship, a dynamic model of the shaft-cylindrical roller-bearing-pedestal system is established in this paper. Then, the vibration response of the system is simulated by Runge–Kutta algorithm and measured by experiment. Finally, the effects of load and speed, damage size, and radial clearance on the dynamic performance are investigated. The simulation and measurement results indicate that the load F and the speed N can promote the enhancement of the vibration acceleration signal. As the damage length continues to increase, the ring in the Poincaré map begins to break, and the system transits from quasi-periodic to chaotic motion. The vibration signal is more affected by the damage size than by the damage location. When the radial clearance increases from 5 × 10−6 m to 15 × 10−6 m, the PTP value increases from 23.83 m·s−2 to 61.36 m·s−2.