The Accreditation Council for Graduate Medical Education (ACGME) orthopaedic milestones require detailed, frequent resident evaluations. This institution desired a cost-effective objective structured clinical examination (OSCE) to facilitate these evaluations. Data were collected as a prospective, uncontrolled observational study. The OSCE was completed by residents entering and exiting the foot and ankle rotation during postgraduate years 2 and 4. Physician assistants functioned as standardized patients. Statistical analyses were performed using paired and independent t tests. The OSCE was implemented using reliable, low-cost modalities and has facilitated milestones evaluations. Preliminary data show 4th-year residents performed higher in prerotation global assessment with a standardized patient and written exam (p < .03). Second-year residents showed improvement in the written exam on rotation completion (p = .03). Using this methodology, institutions may establish similar cost-effective OSCEs as feasible evaluative solutions to satisfy milestone requirements. The authors believe this tool may be modified for any specialty. (Journal of Surgical Orthopaedic Advances 26(4):257-261, 2017).