This study examined the relationship between academic preparation and post-secondary educational outcomes. To uncover the factors that influence secondary-level school course-taking patterns and outcomes, multi-level modelling was conducted using data from a nationally representative sample of US secondary-level school students from the Education Longitudinal Study of 2002. Results indicated (1) significant effects from student, family and school predictors on course-taking patterns and (2) significant effects from course-taking patterns on enrollment in post-secondary institution types with math course-taking pattern having the largest impact. Implications for educators and administrators are discussed. (Contains 2 tables.)