High-speed machining is a key issue for current die and mould manufacturing. Though this technology has great potential for high productivity, tool wear accelerated by high cutting speeds and hard materials is a barrier. In this work, we attempted to reduce tool wear by controlling the machining inclination angle between the tool and the workpiece. To do this, the range of cutting angles engaged in the cutting using a ball end cutter is obtained from the boundary lines describing machined sculptured surfaces represented by the cutting envelop condition and the geometric relationships of successive tool paths. Then, the chip cross-sectional area and chip length can be obtained from the calculated cutting edge and the rotational engagement angle. The simulation results showed that a machining inclination angle of 15° was good enough from the point view of machineability, and this value was verified by a cutting experiment using high-speed ball end milling.