Shoe with leather upper such as safety and golf shoe requires a roughing process where the upper is roughed fur helping outsole to be cemented well. It is an important and basic process for production of leather shoe but is not automated yet. Thus, there are problems that the defect rate is high and the quality of roughed surface is not uniform. In order to solve such problems, the interest in automation of roughing process is being increased and this paper introduces CAM system for 5-axis automatic roughing machine as one part of automation of roughing process. The CAM system developed interpolates a B-spline curve using points measured from the Roughing Path Measurement System. The B-spline curve is used to generate the tool path and orientation data fer a roughing tool which has not only stiffness but also flexibility to rough the inclined surface efficiently. For productivity, the upper of shoe is machined by side of the roughing tool and tool offset is applied to the roughing tool for machining of inclined surface. The generated NC code was applied to 5-axis polishing machine for the test. The upper of shoe was roughed well along the roughing path data from CAM and the roughed surface was proper fur cementing of the outsole.