Background <p>Clerkship evaluations play a critical role in assessing medical student performance and informing residency selection. Prior studies suggest there are gender-related differences in narrative feedback and numerical evaluations of medical trainees; however, findings remain inconsistent across specialties and institutions. This study examined whether preceptor gender and student gender were associated with differences in clerkship evaluation scores.</p> Methods <p>A retrospective analysis was conducted using 6,855 clerkship evaluations from students in the graduating classes of 2022–2024 at a U.S. Osteopathic medical school. Evaluations were completed by 2,425 preceptors across six required clerkships: Family Medicine, Internal Medicine, Obstetrics and Gynecology, Pediatrics, Psychiatry, and Surgery. Associations between preceptor gender, student gender, and evaluation scores were analyzed using generalized linear mixed models, adjusting for academic year and clerkship rotation.</p> Results <p>Preceptor gender was significantly associated with evaluation scores, with female preceptors assigning modestly lower Total Average and Clinical Competence scores than male preceptors (<i>P</i> &lt; 0.0001). Student gender demonstrated smaller effects, with female students receiving slightly higher Total Average scores (<i>P</i> = 0.0260) and Professionalism scores (<i>P</i> = 0.0026). No significant interaction between preceptor and student gender was observed. Clerkship rotation was strongly associated with evaluation scores, with higher adjusted scores in Family Medicine and Pediatrics and lower in Surgery and Internal Medicine.</p> Conclusion <p>Evaluator characteristics and specialty-specific grading cultures appear to influence numerical clerkship assessments. Although findings may be limited by the single-institution design, these results highlight the potential value of increased standardization and target preceptor development to promote equity and consistency in clinical evaluation.</p>