Our aim was to evaluate haptic virtual reality (VR) simulation with repetitive training as a tool in teaching caries removal (CR) and periodontal pocket probing (PPP) skills. For the CR simulation, multilayered virtual models composed of tooth substance, caries, and pulp were developed. Seven students completed three training sessions each, which were scored based on the volume of the cut region, the number of instances of handpiece overload, and total cutting time. For the PPP task, we developed a virtual periodontal disease model and 26 students received training in measuring pocket depth. Pocket probing force was measured and proficiency was evaluated. In the CR task, scores for the second and third training sessions were significantly higher than for the first training session. We likewise obtained effective repetitive training results for the PPP task. Our simulator was effective at teaching hand skills for both tasks within short-term evaluation.