A 7224C high-speed angular contact ball bearing used in a multi-wire sawing machine is selected as the research object to investigate the cage dynamic characteristics under oil-lubricated operating conditions. First, in order to determine the oil-phase volume fraction on the cage surface, a fluid-domain model of the bearing cavity is established, and numerical simulations are performed using the VOF multiphase-flow method coupled with the RNG k-ε turbulence model. The effects of the guiding clearance, pocket clearance, and rotational speed are analyzed, and a regression equation for the cage-surface oil-phase volume fraction is developed based on a uniform test design. Subsequently, a bearing dynamic model is constructed, in which lubrication-related parameters are determined based on the regression equation, and the force balance and equations of motion for each component are derived. Finally, using the slip ratio and the deviation ratio of the cage-centroid whirl velocity as evaluation indices, the influences of multiple parameters on cage stability are examined. The results indicate that increasing the clearances and rotational speed leads to a higher slip ratio, whereas increasing the axial and radial loads reduces the slip ratio. Moreover, enlarging the guiding clearance and increasing the axial load improve cage stability, while a larger pocket clearance and an excessively high radial load deteriorate cage stability.