Wear and rolling contact fatigue (RCF) defects are most important causes of rail damage, and often interaction competitive at present railway track. Head check is one of rolling contact fatigue (RCF) defects, and generally occurs in mild circular curves and transition curves that are set at both ends of sharp circular curves. Wear tends to limit the crack growth of head checks by removing the material from the RCF surface. In order to clarify the conditions of the occurrence and growth of head checks, the authors measured the interacting forces between wheels and rails and the angle of attack of wheelset, and carried out contact analyses using the actual profile data of wheels and rails. The effects of the lateral force, the contact geometry, and the wear rate at rail gauge comer on the formation of head checks were also analyzed by using the worn profiles of actual wheels and rails and the data obtained by a track inspection car. Some specific range of wear rate at the gauge comer was identified as having close relation with occurrence of head checks.