This paper aims to describe the effect of tool geometry on cutting characteristics of a 1.0 mm thickness acrylic worksheet subjected to a punch/die shearing. A set of side-wedge punch and side-wedge die which had the edge angle of 30°, 60° and/or 90° was prepared and used for cutting off the worksheet. A load cell and a CCD camera were installed in the cutting system to investigate the cutting load resistance and the side-view deformation of the worksheet. From experimental results, it was revealed that a cracking pattern at a sheared zone was remarkably affected by the edge angle of cutting tool. A cracking direction was almost coincident to the edge angle when considering the punch/die edge angle of 30°, while any matching of them was not observed in case of the punch/die edge angle of 60°, 90°. By using the 30° side-wedge tool, a flat-smooth sheared surface was generated. When combing the punch edge angle of 90° and the die edge angle of 60°, the cracking profile was characterized by the both edge angles for each part (die and punch). Carrying out an elasto-plastic finite element method analysis of cutter indentation with a few of symmetric and asymmetric punch/die edges, the stress distribution and deformation flow at the sheared zone were discussed with the initiation of surface cracks.