The procedure for the head check initiation life prediction of railway rails has been developed. It is mainly performed by three-dimensional finite element (FE) analyses that account for the local material response generated by the contact load between wheel and rail. Both wheel and rail are modeled by FE mesh, and the wheels are loaded then rotated to the rolling direction on the rails repeatedly. The Chaboche and Lemaitre model is used to simulate the material response that is important in rolling contact situations. The results obtained from FE analyses are combined with the theory of critical distance and the critical plane approach to predict fatigue crack initiation life in the railhead. Parametric studies are performed to investigate the influence of several factors on the crack initiation life. Finally, the predictions are compared with the data obtained from the investigation in the field.