Dynamic behaviors of ball-type contact surfaces under unbalanced bending loads are studied using point-to-point analysis, three-dimensional finite element simulation based on the Hertz Contact Theory, and a modal test. Results derived from these models are very similar but the Finite Element Model provides the best results since it allows for more elements of study, such as the steel ball, carriage, rail etc. In the study, results also show that frequencies vary slightly, but there is an obvious change in shapes. Therefore, the contact stiffness in simulations must be properly selected with the conclusion that different external loadings may affect the dynamic characteristics of such structures significantly.