In this paper, a Drill Point Simulation System (DPSS) which is being developed at Northeastern University is presented. By means of DPSS, the geometric models of the helical drill points were shown after inputting their design parameters. Then, the grinding parameters of the helical drill points were produced. According to the grinding parameters, the helical drill points were ground by the SD helical drill point grinder which was developed at Northeastern University. Furthermore, drilling tests were performed on aluminum sheet workpieces to investigate drilling performance of the helical drill points. In addition, the relationships between the geometric parameters of helical drill points and their grinding parameters also were derived.