IMPORTANCE Women are underrepresented in medical leadership positions; however, representation of women among academic oncology leadership is unknown. OBJECTIVES To evaluate representation of women overall and in leadership positions in academic medical oncology (MO), radiation oncology (RO), and surgical oncology (SO) programs and to examine the association of women leadership with overall faculty representation of women per program. DESIGN, SETTING, AND PARTICIPANTS In this cross-sectional study, MO, RO, and SO training program websites were queried from October 2018 through June 2019. All faculty from 265 of 273 accredited MO, RO, and SO training programs (97.1%) were included. EXPOSURE Gender. MAIN OUTCOMES AND MEASURES Observed proportions of women in leadership positions compared with the expected proportion of overall women faculty in MO, RO, and SO were assessed. Rates of representation of women across each MO, RO, and SO program's faculty based on the presence or absence of a woman in a leadership position were compared.