The invention discloses a tool damage detection system which comprises a working drum, a working housing, tools and tool aprons, wherein the tools are arranged on the working drum through the tool aprons; the working drum is arranged in the working housing. The tool damage detection system also comprises an infrared videography module, a data processing module and a feedback terminal. According to the tool damage detection system, in a working process of the tools, the temperatures of the tools are obviously higher than that of the surrounding environment; therefore, the infrared videography module arranged on the working housing can be used for recording the shape of a tool; the shape information is processed by the data processing module and then is finally fed to an operator through the feedback terminal, so that the damage condition of the tool can be detected. The tool damage detection system can find defects immediately in a detection process and is high in detection efficiency; a contour image of the tool under high temperature can be acquired through infrared videography, and a detection result is accurate. The invention also discloses a tool damage detection method and engineering machinery provided with the tool damage detection system.