Serviceability and running safety of the high-speed train on/through a bridge are of major concern in China. Due to the uncertainty chain of the train dynamic analysis in crosswinds originating mainly from the aerodynamic assessment, this paper primarily reviews five meaningful progresses on the aerodynamics of the train-bridge system done by Wind Tunnel Laboratory of Central South University in the past several years. Firstly, the flow around the train and the uncertainty origin of the aerodynamic assessment are described from the fluid mechanism point of view. After a brief introduction of the current aerodynamic assessment methods with their strengths and weaknesses, a new-developed TRAIN-INFRASTRUCTURE rig with the maximum launch speed of 35 m/s is introduced. Then, several benchmark studies are presented, including the statistic results of the characterized geometry parameters of the currently utilized bridge-decks, the aerodynamics of the train, and the aerodynamics of the flat box/truss bridge-decks. Upon compared with the foregoing mentioned benchmarks, this paper highlights the aerodynamic interference of the train-bridge system associated with its physical natures. Finally, a porosity- and orientation-adjustable novel wind barrier with its effects on the aerodynamics of the train-bridge system is discussed.