A follow-up study of children who began school at age 4 (referred to as Year 1 in this study) was conducted to examine the influence of three different preschool models on later school success. These children from an urban school district were studied again in Year 5 as they prepared to leave the primary grades and in Year 6 when they were scheduled to enter fourth grade if not previously retained. The study examined report card grades, retention rates, and special education placement of 160 children at the end of their fifth year in school and 183 children at the end of their sixth year in school. The sample was 96% African American and 54% female, with 75% of the children qualifying for subsidized school lunch and 73% living in single-parent families. Academically, girls surpassed boys at the end of Year 5, and this difference persisted into the next grade level. Children whose preschool experience was more academically directed had been retained less often than peers. No differences attributable to preschool model were found for special education placement. By the end of children's fifth year in school, there were no significant differences in academic performance of children who had experienced three different preschool models. By the end of their sixth year in school, children whose preschool experiences had been academically directed earned significantly lower grades compared to children who had attended child-initiated preschool classes. Children's later school success appears to have been enhanced by more active, child-initiated early learning experiences. Their progress may have been slowed by overly academic preschool experiences that introduced formalized learning experiences too early for most children's developmental status.