Derivative cutting is a texture-edge cutting of chip bottom side, which happens all the time in machining with textured tools. Two new types of textured tools are developed and fabricated: a micro-textured tool with chamfered texture edge (CTE) tool and a multiscale textured (MSTT) tool with the texture surface below the rake face. The effectiveness of the tools on inhibiting derivative cutting is investigated at different cutting velocities. For the CTE tool, the inhibiting effect is more pronounced with the increase in the chamfer angle, but the severe rake face wear eventually leads to the occurrence of derivative cutting. Compared with the CTE tool, the multiscale textures of the MSTT tool provide more sustainable effectiveness in inhibiting derivative cutting. The inhibition mechanisms of the two types of textured tools are discussed.