This paper investigates the influence of wheel defects on the development of rail defects up to a state where rail prompt replacement becomes necessary taking into account different models of the dynamic contact between a wheel and a rail. In particular, the quasistatic Hertz model, the linear elastic model, the elastoplastic Kilchevsky model, the elastoplastic Aleksandrov-Kadomtsev model, the viscoelastic model with unloading, and the viscoelastic model with the Riemann-Liouville fractional derivatives are used for the analysis. During the motion of a railway vehicle, the wheel pair position in relation to rails changes significantly, which causes various combinations of wheel-rail contact areas. Even provided the constant axial load, the normal stresses will substantially change due to the differences in the radii of curvature of contact surfaces of these areas, as well as movement velocities of railway vehicles.