The aim of this study was to evaluate the process of student self-assessment on operative dentistry skills across four years at the University of Louisville School of Dentistry. First, a retrospective analysis of the Class of 2016 students' self-assessment and faculty assessment grade sheets was conducted to determine mean differences and correlations across time. Both preclinical (D2: n=120) and clinical (D3: n=120; D4: n=120) grade sheets were evaluated. Second, 25 students from each of the D1, D2, D3, and D4 classes in 2016 were asked to evaluate dentoform work, and 25 operative calibrated faculty members graded the same two dentoforms. The results of the retrospective analysis were that the D2 students' self-assessment scores were significantly higher than the faculty scores (t-test; p<0.05), and there was a negative correlation of scores (r=-0.503). The D3 students' self-assessment scores were also significantly higher than the faculty scores (t-test; p<0.05), and there was a negative correlation (r=-0.235). The D4 students' self-assessment scores were not significantly different from the faculty scores (t-test; p>0.05), and there was a positive correlation (r=0.408). In the prospective analysis, the D1, D2, and D3 students graded the dentoforms significantly higher (ANOVA; p<0.05) than did the D4 students and faculty members. There was an increasing correlation of scores directly related to experience (D1: r=-0.120; D2: r=0.255; D3: r=0.352; D4: r=0.689). These results support the concept that students' self-assessment is a learned process through experiential and continual encounters across time. The summative goal for all dental schools is to provide students with the skills and knowledge to critically evaluate their work for self-directed learning.