This retrospective study of 535 children and their primary caregivers focuses on factors that influence age appropriate school entry and grade progression. The children studied live in a peri-urban community in Kampala, Uganda and were eight years old at the time of the study. The study examined the influence of family variables, home life stress events, exposure to early childhood development (ECD) services on age at school entry and educational grade transitions of young children. This is very useful given the relative lack of African studies of this size and nature. Descriptive and correlational, as well as regression analyses, are included in the findings. The major findings from this study are: status of caregivers, ECD history, child age at ECD enrolment, type of ECD attended, life stress events in the household, are significantly related to children school status and progression.