The authors examined long-term outcomes for children who experienced delayed entry to kindergarten or kindergarten retention. They used a cohort of 6,841 students to compare these groups to each other and typically progressing peers. First, the authors compared the groups on demographic and early childhood variables. For the long-term school-based outcomes, they used propensity score analysis to address pretreatment differences between groups and examined outcomes by free or reduced-price versus paid lunch status. Results showed that the retained group experienced greater early risk than the delayed entry and typically progressing groups and poorer long-term outcomes even when controlling for pre-existing differences. Other than placement in special education, few differences emerged between the delayed entry and typically progressing groups. Implications of the study for progression decisions are discussed.