We investigate whether the career opportunities afforded to aspiring principals have become more equitable over time. Controlling for a wide variety of individual and contextual characteristics, we employ discrete-time hazard modeling to predict the probabilities of teachers at the various intersections of race and sex entering the principalship. We then calculate group means of these predictions, which are collapsed over academic years. Results indicate that the likelihood of women entering the principalship, while having improved in recent years, still lags behind those of men. Investigation of gaps constructed round the intersectionality of race and sex reveal a historically rigid status quo, whereby White educators, both male and female, have maintained a substantial advantage in the pathway to the principalship.