Diamond core drills are applied to drill difficult-to-cut materials. This paper proposes basic understanding of ceramic drilling mechanics and characteristics of main factors affecting tool life, tool wear, cutting force, and chipping thickness. In contrast to conventional drilling, the core drilling process make deep grooves on the workpiece. One difficulty of it is the evacuation of chips from the drilled groove. As the drilling depth increases, an increased amount of chips tend to cluster together and clog the groove. Eventually severe wear develops and diamond grits are separated from the drill body. To relieve the clogging problem and to evacuate chips from the groove easily, the helical drilling process is applied for the core drilling process. To analyze drilling characteristics and derive optimal drilling conditions, tool life, tool wear, cutting force, and chipping thickness are quantified through the monitoring system and the Taguchi method. Mathematical models for the tool life and chipping thickness are derived from the response surface method. Optimal drilling database has been constructed through the experimental models.