Abstract: The overhead contact system (OCS), as a typical ancillary facility of the tunnel, is normally subjected to the repeated wind loading generated by the high-speed train passing through the tunnel. In order to accurately evaluate its operational safety, analyzed are the dynamic amplification effect of the cantilever bracket under the wind loading of the train and the induced damage in the concrete anchorage end. Based on computational fluid dynamics (CFD) analysis, obtained is the three-dimensional space-time distribution of train wind as the train passes through the tunnel at high speed, and carried out is the correlation analysis between the tunnel longitudinal wind speed and the train wind loading on the OCS to determine the most critical OCS location and obtain its wind load time history. The static and dynamic finite element analysis (FEA) is conducted on the cantilever structures to calculate the structural dynamic amplification factor with different OCS size parameters, including different horizontal connection angles of stay rod and cantilever connection distances, using the critical train wind loading. Considering the dynamic amplification factor, the nonlinear FEA is used to obtain the damage and failure of the anchorage concrete under external loads. The results show that: there is a strong quadratic relationship between tunnel longitudinal wind speed and wind loading on the OCS, and the most critical wind loading exists on OCS near the tunnel exit. The amplification factor in different analysis models is at least 1.358, and the maximum is at 1.556. Under the action of bolt pretightening force, of self-weight and normal loading of the OCS, and of train wind loading, there are micro-cracks initiated in the anchor concrete near each bolt hole within a certain depth. Specifically, the concrete near the bolt hole on the windward side and cantilever positive direction has a peak value of tensile damage factor of 0.769 and, a peak value of compressive damage factor of 0.365. In addition, the contribution of the train wind to the internal force of the anchorage structure is not greater than 13.63%. The research results will serve as a reference for the design of the OCS, the damage analysis of the lining concrete and its maintenance and reinforcement.