Rail transportation is regarded as a reliable, quick, and secure mode of transportation. The wheel-rail contact interaction is crucial to the railway operation since it is responsible for supporting, traction, braking, and steering of railway vehicles. Improper wheel-rail interactions may produce or exacerbate wheel-rail interface issues such as rolling contact fatigue (RCF) and wear, which can threaten the vehicle’s running safety and stability. A review of the evolution and recent literature on wheel-rail contact mechanics and tribology is presented here. Topics covered include the basics of wheel-rail contact problem and methodologies for modeling both the normal contact (Hertzian and non-Hertzian) and tangential contact (Kalker’s theories including CONTACT and FASTSIM algorithms, Polach’s theory, USETAB program, etc.). The paper also reviewed various effects of contaminants and environmental conditions (water, leaves, sand, temperature, humidity, etc.) in wheel-rail contact. Various wheel-rail empirical adhesion models like the Water-induced low adhesion creep force model (WILAC) model and adhesion models based on elastohydrodynamic lubrication (EHL) theory (Greenwood-Tripp [GT] and Greenwood-Williamson [GW] models) are also reviewed. Lastly, the paper discusses the need and challenges for developing and integrating the wheel-rail non-Hertz contact model and adhesion model, as well as open areas for further research.