Using data from the Chicago Longitudinal Study (CLS), an ongoing investigation of a panel of low-income minority children growing up in an inner city, this study investigated whether retention is associated with participation in postsecondary education and public aid receipt. The study sample included 1,367 participants whose data were available for grade retention and educational attainment by age 24. Findings from both regression and propensity score matching indicated that grade retention was associated significantly with lower rates of participation in postsecondary education. Late retention (between fourth and eighth grades) was linked more strongly to lower rates of post-secondary education than early retention (between first and third grades). There was no significant association between retention and public aid receipt. (Contains 7 tables and 1 figure.)