This paper presents the identification of damages and stress analysis of rail/wheel rolling contact region. The railhead surface of used rail track was investigated to identify damages and the hardness of the rail/wheel contact area was measured. Finite element method FEM code, ANSYS was used to determine the stress distribution at vicinity of rail/wheel contact area. The results showed that the hardness increased on the contact area between rail and wheel due to repeated rolling contact of rail and wheel surface. Severe damages and cracks were observed on the railhead surface and in the cross section of the rail at the contact region. The FEM simulation showed that the highest stress distribution regions were matched with the area of severely damage and high hardness obtained from the observation and experimental results.