Background: Self-assessment, crucial skill in professional practice, is essential for dentists to deliver patient care. Teaching self-assessment in dental education prepares students for this role. Structured self-assessment refers to self-assessment guided by a predefined criterion-based checklist. This study aimed to evaluate the impact of structured checklist on First-year dental students' self-assessment and dental carving skills. The study also aimed to assess the influence of the checklist on faculty assessment. Methods: A prospective cohort study was conducted involving 32 first-year dental students. Participants completed two carving exercises: Exercise 1 (self-assessment without a checklist) and Exercise 2 (self-assessment with a checklist). Student self-assessments were compared with faculty assessments. Statistical analyses, including paired t-tests and effect size calculations, were performed. Student perceptions were assessed via a survey. Results: In Exercise 1, a significant discrepancy was observed between student self-assessments and faculty assessments (p = 0.002). In Exercise 2, alignment between student and faculty assessments significantly improved (p = 0.001). Inter-exercise comparisons showed a significant increase in student self-assessment scores with the checklist (p < 0.001). Furthermore, the increased faculty assessment scores in Exercise 2 indicate a tangible improvement in carving skills. Survey results indicated positive student perceptions regarding the checklist's usability and effectiveness. Conclusions: Structured self-assessment significantly improved the accuracy of student self-evaluations and may have contributed to the students' enhanced dental carving skills. This approach offers a valuable tool for preclinical dental education, promoting objective self-assessment and skill development.