A nonlinear dynamic model is proposed to investigate the dynamic interactions between the rolling element and cage under rotational speed fluctuation conditions. Discontinuous Hertz contact between the rolling element and the cage and lubrication and interactions between rolling elements and raceways are considered. The dynamic model is verified by comparing simulation result with the published experimental data. Based on this model, the interaction forces and the contact positions between the rolling element and the cage with and without the rotational speed fluctuation are analyzed. The effects of fluctuation amplitude, fluctuation frequency, and cage pocket clearance on the interaction forces between the rolling element and the cage are also investigated. The results show that the fluctuation of the rotational speed and the cage pocket clearance significantly affects the interaction forces between the rolling element and the cage.