At high speeds, skew and skid may frequently occur for the rollers in cylindrical roller bearings, especially when under eccentric load, as the uneven load distribution along the generatrix of the roller further aggravates this phenomenon. In this paper, a dynamic model of a cylindrical roller bearing was established, taking into account roller skewing and interactions with the cage. Firstly, the interaction between the roller and the raceway was calculated by slicing the roller along its generatrix. Furthermore, the computation of the interaction between the roller and the cage is based on elastic theory, taking into account pocket clearance. Subsequently, the dynamic equations for both rollers and cage were derived. Based on this foundation, an investigation was conducted to reveal how rotational speed, radial loads, and moment loads affect roller slipping, skewing characteristics, and interactions with the cage under uneven load conditions. The findings indicate a direct proportionality between roller slipping and bearing speed while exhibiting an inverse relationship with load magnitude. Additionally, it was observed that both bearing speed and load have a direct influence on roller skewing angle. Moreover, normal interaction force between the roller and cage demonstrates a direct proportionality to bearing speed while inversely correlating with load magnitude.