ABSTRACT Purpose This study evaluated the effectiveness of combining a digital real‐time evaluation system and virtual simulation system in enhancing tooth preparation skills for preclinical training. Methods A total of 32 students from the Class of 2020 were trained using the traditional phantom head simulator. In contrast, 28 students from the Class of 2021 and 32 students from the Class of 2022 completed the training and the first ceramic crown preparation test and were assigned to Groups A or B, receiving training either with the digital real‐time evaluation system or with the virtual simulation system, respectively. After completing the second incisor crown preparation test, training tasks were exchanged for a month, concluding with a final incisor crown preparation test and questionnaire. Students from the Class of 2022 completed a multidomain well‐being survey to evaluate their perceived stress levels and overall well‐being. Results The 2021 and 2022 cohorts scored significantly higher than the 2020 cohort in the final test. Groups A and B (the 2021 and 2022 cohorts) showed statistically significant sequential improvement across the three tests. However, no significant difference was observed between the performance of Group A and Group B in any individual test ( p > 0.05). Students expressed stronger support for the implementation of the digital real‐time evaluation system relative to the virtual simulation system. Conclusions The combination of the digital real‐time evaluation system with virtual simulation system enhances the manual dexterity of dental students in ceramic crown preparation. The sequence in which these two digital methods are implemented does not influence the effectiveness of preclinical tooth preparation training, suggesting that this combined approach may serve as a flexible and effective strategy for preclinical education. A positive association was observed between students’ final test scores in tooth preparation and their emotional well‐being.