Background: The importance of effective mentoring in career success is universally accepted but has not been well studied in academic medicine. Purposes : The purpose was to describe a formal mentoring program of residents by faculty in obstetrics and gynecology and assess professional and educational outcomes. Methods: In 2006, a formal mentoring program was developed. Faculty and residents were provided instruction. Residents selected their mentors and met regularly. Resident–mentor contracts were signed. Mentors developed corrective plans and monitored residents with problems. Outcomes were measured prospectively. Results: Twenty-five residents and 18 faculty participated. After 2 years, 7 residents (28%) had scientific publications as compared to 10% in the year preceding the mentoring program. Eleven (44%) presented oral or poster presentations, and 17 (68%) were conducting scientific research. Mentors' effectiveness was rated between 4.3 and 4.7 (Likert scale of 1–5). Three of 4 residents in remediation fulfilled their educational requirements. Four residents noted insufficient meeting time. Conclusion: A simple but well-organized mentoring system can be an effective means of improving resident learning and enhancing their academic portfolio. Mentoring should be strongly encouraged for residents, especially those with specific deficiencies.