Contact fatigue damages on the rail surface, such as head checks and squats are a growing problem. The fatigue cracks forming on the contact surface grow according to load and lubricating conditions and may end up breaking the rail. Rail fracture can be avoided by preventing the cracks from reaching the critical length. Therefore, the crack growth rate needs to be estimated precisely according to the conditions of the track and load to develop a maintenance plan against rail damages. Therefore, it is important to understand the mechanism of cracks initiation and growth on a rail due to repetitive rolling contact. In this study, we have investigated the crack growth behavior on the rail surface by using the twin-disc tests and the finite element analysis.