Background: Female underrepresentation in academic medicine leadership is well-documented; however, oncology specific data are scarce. This study evaluates female leadership representation in academic medical oncology (MO), radiation oncology (RO) and surgical oncology (SO) programs. Furthermore, we examine the impact of female leadership on overall female faculty representation. Methods: A total of 264 (96%) Accreditation Council for Graduate Medical Education actively accredited MO [144 of 153], RO [93 of 94] and SO [27 of 27] training programs were included. The gender of overall faculty and those in leadership positions (program director and departmental chair/division chief) of each program was determined using hospital websites from 10/01/18 to 01/27/19. The chi-squared goodness-of-fit test was used to examine whether the observed proportion of females in leadership positions deviates significantly from the expected proportion based on the actual proportion of overall female faculty in MO, RO and SO. Two-sample t-tests were used to compare rates of female faculty representation across each program based on the presence/absence of female in a leadership position for MO, RO and SO. Results: Female faculty representation in MO, RO and SO was 37.1% (1,554/4,191), 30.7% (389/1,269) and 38.8% (212/546), respectively. Female representation in leadership positions was 31.5% (82/260), 17.4% (31/178) and 11.1% (5/45), respectively. The observed proportion of females in leadership positions was significantly lower than the expected proportion of females in leadership positions for RO (17.4% vs. 30.7%, p = .0001) and SO (11.1% vs. 38.8%, p = .0001), and demonstrated a trend towards significance for MO (31.5% vs. 37.1%, p = .063). 47.9%, 33% and 18.5% of MO, RO and SO programs had ≥1 female in a leadership position, respectively. Programs that had a female in a leadership position had a higher mean percentage of overall female faculty than those that did not: 41.0% vs 35.0% (p = .0006), 36.0% vs 26.0% (p = .0002) and 39.0% vs 32.0% (p = .348) for MO, RO and SO, respectively. Conclusions: Gender disparity exists in academic MO, RO and SO faculty and is magnified at the leadership level. Programs with a female physician in a leadership position are associated with a higher percentage of female faculty.