The water chamber head is made of 508III steel with high strength and hardness. The cemented carbide tool bears a large thermal-mechanical load during the cutting process, which leads to severe insert wear and damage as well as low tool life. Firstly, the milling experiments and finite element (FE) simulation were carried out to study the thermal-mechanical characteristics of tools. Secondly, the thermal-mechanical coupling simulation was carried out to explore the temperature field, strain, total deformation of the milling cutter, and the deformation and strain of the rake face of the milling insert respectively. Finally, the tool wear experiment was carried out, and the form, morphology, and energy spectrum of tool wear were analyzed, and the parameters of the crater wear were measured. The proposed crater wear rate was used as the characterization variable of tool wear, and the crater wear rate model was established to explore the wear evolution process of inserts preliminarily. The research results can provide theoretical support and experimental basis for the in-depth study of the tool failure mechanism and tool optimal design of the high-efficiency milling water chamber head.