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Objective. To explore whether metacognition can be improved in Doctor of Pharmacy (PharmD) students through routine self-assessment over a year-long advanced pharmacy practice experience (APPE) sequence. Methods. Differences between self-assessment scores and preceptors' scores for three cohorts of pharmacy students between 2015 and 2018 were compared between the first, second, and third trimester to determine whether students more accurately evaluated their performance over time. The primary endpoint was change in the absolute difference between student and preceptor evaluation (rubric and composite scores) between trimesters. Results. Of 2577 student and preceptor evaluations eligible for inclusion, 1713 were completed, matched, and analyzed. Using the same rubric as preceptors, students overestimated their performance by an average of 16 points during the first trimester, followed by 14 and 12 points during the second and third trimester, respectively. This reflected a significant improvement over time. No significance difference was found between student and preceptor composite scores. Faculty preceptorship, students' pre-APPE grade point average, and type of APPE were not associated with any difference in rubric or composite scores. Conclusion. This analysis revealed that the difference between student self-evaluation grades and preceptor evaluation grades was greatest during the first trimester and significantly decreased in the second and third trimesters. This could reflect students' development of metacognitive processes over time. Metacognition is a vital skill for pharmacy students to learn, and opportunities to develop this skill should be incorporated throughout the pharmacy curricula.