In the present paper, the wear and breakage mechanisms of coated carbide tools are investigated in milling of H13 steel (HRC 30-35) and SKD11 hardened steel (HRC 58-62). The experiment results indicate that the hardness of workpiece has a dominant effect on tool failure patterns. Due to the low hardness of H13 steel, low-stress-repeated impact load on the tool induces the generation of cracks, but not enough to cause tool fracture. Thus, tool failure pattern is flank wear in milling of H13 steel. In contrast, the high-stress-repeated impact load facilitates the initiation and propagation of cracks and ultimately leads to breakage of rake face when milling SKD11 hardened steel. The geometry model of tool wear and breakage is established to explore the variation of tool angle. It is found that the flank wear reduces the clearance angle, while the breakage of rake face decreases the rake angle. In addition, the effect of tool wear and breakage on the cutting forces and chip formation is studied. The flank wear increases the friction coefficient between tool and H13 steel, and the breakage of rake face increases chip deformation and reduces the sharpness of cutting edge, both of which result in the increase in cutting forces. Furthermore, the wave-shaped chips are formed throughout milling of H13 steel, while the breakage of rake face results in the curling and separation of sawtooth chips when milling SKD11 hardened steel.