Mechanical components applied in ore crushing, the drilling of oil wells, and soil plowing need to be manufactured from materials with high resistance to abrasive wear, erosion, and corrosion. Typical materials applied under these severe conditions are cold work tool steels, high-speed steels and high-Cr white cast iron (HCWCI), which present a challenge in machining. In milling, the cutting fluid can easily access the cutting region due to interrupted cutting. In this context, coated cemented carbides associated with lubricooling techniques may be an alternative to improve the process feasibility. The aim of this study was to evaluate the effects of different coated cemented carbide grades and lubri-cooling techniques on the tool life and surface residual stress of the milled surface of HCWCI. Therefore, two coated cemented carbide grades associated with two lubri-cooling techniques (flood emulsion and liquid nitrogen—LN2) were applied in milling tests. The results demonstrated the feasibility of using the coated cemented carbide as a tool material in the milling of HCWCI (cutting time longer than 15 min). Furthermore, LN2 increased, by at least a factor of 2, the tool life when compared with flood emulsion. Regarding the milled surface, values above 500 MPa were obtained for the compressive residual stresses with the use of the worn cutting edges and the application of LN22030