<h3>Study Objective</h3> To describe the proportion of female faculty in departmental administrative and educational leadership roles in Obstetrics and Gynecology departments. <h3>Design</h3> Cross sectional observational study. <h3>Setting</h3> Accredited Obstetrics & Gynecology residency programs. <h3>Patients or Participants</h3> 288 accredited residency programs were identified from 2019 to 2020 with 1237 individuals in leadership positions. <h3>Interventions</h3> Similar to a 2012-2013 survey by Hofler et al., residency program websites and corresponding fellowships (Maternal Fetal Medicine, Female Pelvic Medicine and Reconstructive Surgery (FPMRS), Reproductive Endocrinology and Infertility (REI), Gynecologic Oncology), departmental, and divisional websites were queried for those in administrative and educational leadership positions. Information regarding gender (as determined by surrogates of name and photographic gender expression), medical and academic degrees, academic rank, and subspecialty certification was abstracted. <h3>Measurements and Main Results</h3> Within administrative leadership roles, women comprised 29% of chairs, 46% of vice chairs, and 47% of division directors; women held significantly fewer chair positions than men (p <.001). In educational leadership, women made up 71% of medical school clerkship directors, 58% of residency directors, and 50% fellowship directors. Women were more likely to hold educational leadership positions (56% vs 40%, p<.001) while men were more likely to hold administrative leadership positions (68% vs 52%, p <.001). There was greatest gender equity within FPMRS and least gender equity in Gynecologic Oncology and REI. Female leaders were more likely to have received additional academic degrees (ex. MBA, MPH) than their male counterparts (19% vs 13%, p=.002). <h3>Conclusion</h3> Women continue to be underrepresented in administrative leadership positions. Compared to 2012-2013, there is only a 9% increase in proportion of women chairing and 10% vice chairing Obstetrics and Gynecology departments; the increase is more substantial in other positions, such as division directors (17%). Our findings demonstrate ongoing gender disparity in the highest levels of departmental leadership and the need to further improve upon diversity and gender equality within leadership roles.