Abstract: The rolling contact issue between wheel and rail is analyzed in this paper. The randomness of the contact position which can be described by normal distribution in the rolling process is pointed out. On this basis, the contact points of wheel surface are numbered, and the discrete sample space is formed using these discrete points. The contact probability of each contact point in each cycle of wheel rolling is approximately calculated by using normal distribution method. A method for calculating the contact point position, contact times, and contact stress of wheel surface in the process of wheel/rail rolling contact is constructed by using previous studies, calculating the contact point position and contact stress between the LM-type worn tread wheel and the CHN60 rail. Furthermore, the line is simplified and each section is numbered. The fatigue damage accumulation hypothesis and the fatigue curve equation are adopted to establish the mathematical model for calculating the fatigue life damage of wheel surface contact points on the actual railway. In addition, a calculation example of a specific railway is carried out. The regulation change of wheel contact points with the lateral displacement of wheelset is obtained. The rolling contact fatigue damage of the wheels at different contact positions is calculated and analyzed when the train vehicles travel on straight lines and curve sections. The theoretical fatigue life is also calculated. An example study shows that the fatigue damage of the wheel on the outside of the curve is obviously much more serious than that of the inner wheel. Contact times and contact stress need to be comprehensively considered to analyze rolling contact fatigue failure of the wheel surfaces.