This retrospective study of 535 households with 8-year-old children focuses on factors that can influence age-appropriate school entry and subsequent grade-level progression. The households included in this research are from a peri-urban community near Kampala, Uganda. Data were collected mainly from primary caregivers. The study examined the influence of family variables, home environment, stressful life events, and exposure to early childhood development (ECD) services on both age at school entry and educational grade level. Given the relative lack of African studies of this size and nature, descriptive and correlational analyses, as well as a regression analyses, are included in the findings. From the regression analyses, three major findings emerge. First, family structure (intact vs. other) and educational level of the caregiver are important variables in predicting children's enrolment in ECD, age of entry into school, and grade level in school. Second, whether the child attended ECD or not, the child's age at ECD enrolment, and the type of ECD attended are significantly related to school attendance, that is, if currently in or out of school and grade level achieved in school. Third, stressful life events in the household are significantly related to the grade-level progression of children in school.