In Israel, despite increasing numbers of women in medical training, there remains a scarcity of female representation in leadership positions within academic medicine. This cross-sectional study investigates the proportion of women holding departmental chair positions in Gynecologic Oncology in Israel and conducts a comparative analysis with the United States (USA) in 2022. Data was gathered from Internet websites regarding personnel staff and chair positions in Gynecologic Oncology departments in Israel and from USA medical centers with Gynecologic Oncology Fellowship programs reported by the Society for Gynecologic Oncology (SGO). The representation of women in chair positions in Israel was lower compared to the USA, 4 (19.0%) vs. 28 (45.9%), Odds Ratio 95% Confidence Interval 0.27 (0.08–0.92), p = 0.038. The findings highlight a significant gender disparity in senior Gynecologic Oncology positions in Israel compared to the USA, necessitating a thorough investigation of the underlying reasons and the implementation of efforts to address this gender bias and promote gender equality in Gynecologic Oncology and across all fields of medicine.