Background: The anatomy curriculum has undergone considerable reductions in class time, resulting in decreased student anatomical knowledge retention and confidence during their surgical rotations. To counter this deficit in anatomy knowledge, a clinical anatomy mentorship program (CAMP) was developed by fourth-year medical student leaders and staff mentors in a near-peer teaching fashion prior to the surgical clerkship. This study analyzed the impact this program had on third-year medical students (MS3s) self-assessed anatomical knowledge and confidence in the operating room on the Breast Surgical Oncology rotation after this near-peer program. Methods: A single-center prospective survey study was performed at an academic medical center. Pre- and post-program surveys were administered to all students who participated in the CAMP and rotated on the breast surgical oncology (BSO) service during the surgery clerkship rotation. A control group of individuals who did not rotate on the CAMP was established, and this group was administered a retrospective survey. A 5-point Likert scale was used to assess surgical anatomy knowledge, confidence in the operating room, and comfort in assisting in the operating room. Control group versus post-CAMP intervention group and pre- versus post-CAMP intervention groups survey results were compared using the Student’s t-test with a p-value of <0.05 statistically significant. Results: All CAMP students rated their surgical anatomy knowledge (p < 0.01), confidence in the operating room (p < 0.01), and comfort in assisting in the operating room (p < 0.01) as greater than those who did not participate in the program. Additionally, the program improved the ability of third-year medical students to prepare for operating room cases going into their third-year breast surgical oncology clerkship (p < 0.03). Conclusions: This near-peer surgical education model appears to be an effective way to prepare third-year medical students for the breast surgical oncology rotation during the surgery clerkship by improving anatomic knowledge and student confidence. The program can serve as a template for medical students, surgical clerkship directors, and other faculty interested in efficiently expanding surgical anatomy at their institution.