In academia, the proportion of women decreases with each career level. In this research, we examined how this so-called leaky pipeline relates to gender-based relative expectations of success. The participants were students from social sciences where women are the majority among students, such that it is more readily – but erroneously – inferred that gender discrimination is not an issue. We assumed that gender-based relative expectations of success should be predicted by two variables. Women students should experience higher gender-based rejection sensitivity than men students, with gender-based rejection sensitivity mitigating relative success expectations in women, but not in men. Men students should exhibit higher hostile-sexist attitudes toward women than women students, with hostile sexism reducing men students’ but not women students’ relative success expectations. We tested our hypotheses in an (under-)graduate sample of women and men students enrolled in educational or psychological majors (N = 372). Results show that a quarter of the women students expected men to be more successful than women and that proportionately more women than men students indicated that women have worse chances of success than men in the job they aspire to. Women were more concerned about being treated differently because of their gender than men, and men held more sexist attitudes toward women than women, with gender-based rejection sensitivity contributing to women students’ and sexism to men students’ expectation that their own gender group will less likely succeed in their aimed for future job. Implications how the leaky pipeline can be patched are discussed.