Wheel wear is one of the most critical factors affecting the vehicle performances and maintenance costs of railway vehicles. However, previous research has to ignore the initial wheel-rail profiles for the evolution of wheel wear. Therefore, this work investigates the relationship between the evolution of wheel wear corresponding to different initial wheel-rail profiles and vehicle dynamics, wheel-rail deterioration. Firstly, the evolution of wheel wear during a long service period is measured from two high-speed railway trains running on two different lines. Contact geometry, e.g., equivalent conicity and contact pair distribution, are extracted. After that, the influence of wheel wear on the vehicle dynamic performance is studied using a multi-body dynamic software. The calculated contact parameters, e.g., pressure, shear traction, and creepage, are used to analyze the distribution of rolling contact fatigue. Based on the experimental and simulation results, the initial wheel and rail profiles significantly affects the wheel wear pattern, the thin rim wheel has uniform wear, and other wheels occurs hollow wear. The hollow wear can lead to gradual deterioration of vehicle dynamics, which conversely aggravates the wheel reprofiling.