A prospective, observational study was performed to evaluate a pilot orientation curriculum which involved all 7 incoming obstetrics and gynecology residents in June 2012. The objective of this study was to assess how a structured orientation curriculum, which employs an evaluation of baseline competency, affects the confidence of incoming first-year obstetrics and gynecology residents. The curriculum included didactic lectures, online modules, simulation, and mock clinical scenarios. Pre- and post-course surveys were conducted online via SurveyMonkey™ and were sent to all incoming obstetrics and gynecology residents. All seven incoming obstetrics and gynecology residents completed the orientation curriculum which included evaluations at the end of the orientation to assess baseline competency prior to taking part in clinical care. Confidence levels improved in all 27 elements assessed. Statistically significant improvement in confidence levels occurred in cognitive skills such as obstetric emergency management (2.9 vs 3.9, P< .05) and technical skills such as knot tying (3.9 vs. 4.6, P< .05). Certain teaching skills also demonstrated statistically significant improvements. A structured orientation program which improves resident self-confidence levels and demonstrates baseline competencies in certain clinical areas can be valuable for many residency training programs.