A new contact model of finite-length crowned roller bearing, capable of handling lubrication, eccentric load, and misalignment situations, is established in this study. Simulation results of interface pressure, film thickness distribution, flash temperature, and subsurface stress can be obtained with different speeds, misalignment angles, load eccentricity, and roller trimming parameters. It is found that edge trimming can greatly reduce the stress concentration at the edge, and there are optimal trimming parameters to minimize the concentrated stress under normal load and eccentric load. When the eccentric load exceeds a certain angle, the increase in the maximum stress can be very large, which may lead to premature failure of the interface. Meanwhile, the staggering velocity caused by the misalignment of the roller axis also has a certain influence on the distribution of the lubricating film.