The present paper describes an experimental test and a coupled contact-thermal-wear analysis of a railway wheel/brake block system through the braking process. During the test, the friction, the generated heat, and the wear were evaluated. It was found that the contact between the brake block and the wheel occurs in relatively small and slowly moving hot spots, caused by the wear and the thermal effects. A coupled simulation method was developed including numerical frictional contact, transient thermal and incremental wear calculations. In the 3D simulation, the effects of the friction, the thermal expansion, the wear, and the temperature-dependent material properties were also considered. A good agreement was found between the results of the test and the calculations, both for the thermal and wear results. The proposed method is suitable for modelling the slowly oscillating wear caused by the thermal expansions in the contact area.