We present a computational model for investigations of the fracture processes and estimation of the remaining life of solids under their cyclic contact interaction. This model is based on the step-by-step construction of the paths of crack propagation in the contact zone with regard for the operational parameters of tribounit and the characteristics of cyclic crack growth resistance of the materials of its elements. The model is applied for the contact interactions of rolling and fretting fatigue. We study the specific features and causes of the formation of such typical contact fatigue damages as pitting, spalling, dark-spot, and systemic cracking. Using the characteristics of cyclic crack growth resistance of rail steels for transverse shear and tension, we estimate their durability by the development of pitting. The main results concerning this problem for the last decade have been synthesized.