A comprehensive study was carried out to numerically evaluate the ratcheting performance of three high strength pearlitic rail steels under different wheel–rail cyclic rolling contact conditions, i.e. free rolling, partial slip, and full slip conditions, different friction coefficients and different axle loads. The wheel–rail cyclic rolling contact was simulated by repeatedly passing a distributed contact pressure and a distributed tangential traction on the rail surface. This study combined the non-Hertzian contact pressure from finite element analysis with the longitudinal tangential traction from Carter’s theory to simulate the wheel–rail cyclic rolling contact problems. A cyclic plasticity material model considering the non-proportionally loading effect developed recently by the authors was applied to simulate the ratcheting behaviour of rail steels. The ratcheting performance of the rail steels was evaluated by the crack initiation life which was determined from the stabilized ratcheting strain rate and the ductility limit of the rail materials. The numerical results indicate that the crack initiation life decreases with the increase of the normalized tangential traction, the friction coefficient and the axle load for all three rail steels. Among the three rail steels, the hypereutectoid rail steel grade with a lower carbon content provides the best ratcheting performance under higher axle loads such as those used railway transport of mineral products in Australia. Furthermore, the numerical results obtained in this study are in reasonable agreement with the in-service performance of the three rail steels. This indicates that the developed approach has the capacity to evaluate the ratcheting performance of other rail steels under service loading conditions. The outcomes can provide useful information to the development and application of rail steels and the development of effective rail maintenance strategies in order to mitigate rail degradation.