Drawing on the expectancy-value model, the present study explored individual and gender differences in university entry and selection of educational pathway (e.g., science, technology, engineering, and mathematics [STEM] course selection). In particular, we examined the multiplicative effects of expectancy and task values on educational outcomes during the transition into early adulthood. Participants were from a nationally representative longitudinal sample of 15-year-old Australian youths (N = 10,370). The results suggest that (a) both math self-concept and intrinsic value interact in predicting advanced math course selection, matriculation results, entrance into university, and STEM fields of study; (b) prior reading achievement has negative effects on advanced math course selection and STEM fields through math motivational beliefs; and (c) gender differences in educational outcomes are mediated by gender differences in motivational beliefs and prior academic achievement, while the processes underlying choice of educational pathway were similar for males and females.