One of the current trends in dental education is to empower dental students on a global platform using advanced technology. Haptic virtual reality simulation (HVRS) is a relatively new technology in the field of teaching and learning operative dentistry. This study aims to assess the impact of haptic virtual reality simulation (HVRS) on dental students’ psychomotor skills acquisition in preclinical operative dentistry. Class I cavity preparations (CP) were performed at baseline by 21 novice dental students on plastic teeth. Duration of CP was recorded and cavity features were evaluated and scored. Then, students were exposed to HVRS training on CP. Another Class I CP was performed by each student on plastic teeth after HVRS training, then evaluated, and the duration was recorded. There was a statistically significant decrease in CP performance time after HVRS training (p < 0.001) and an increase in the mean total marks of CP after HVRS training (p < 0.001). The change in the students’ performance in the CP displayed a statistically significant improvement after HVRS training in smoothness of the pulpal floor (p = 0.047), pulpal floor direction (p = 0.029), buccal, lingual, and mesial wall direction (p = 0.004, p = 0.025, p = 0.002), mesial and distal wall smoothness (p = 0.01, p = 0.001), internal line angle (p = 0.024), and internal point angle (p = 0.029). Overall improved performance in psychomotor skills was found after HVRS training. It could be beneficial to incorporate HVRS training early in pre-clinical operative dentistry courses as an adjunct to conventional phantom head training.