Previous research has demonstrated a graded relationship between cumulative childhood adversity and adverse later outcomes. Individuals with out-of-home care (OHC) experience constitute a population characterised by both childhood and educational disadvantages. Based on a fifty-year follow-up of a Stockholm cohort born in 1953, the purpose of this study was to examine the associations between cumulative childhood adversity and long-term educational outcomes in this group. The cumulative disadvantage perspective suggests that there would be a negative association, while the disadvantage saturation perspective implies that cumulative adversity would be less consequential for disadvantaged individuals. By means of multigroup path analysis, we furthermore asked whether this association may differ in relation to individuals with child welfare contact (CWC) and to the general population (GP). Adjusting for socioeconomic conditions and cognitive ability, cumulative childhood adversity had a negative influence on midlife educational attainment in the GP. However, it did not seem to influence the educational outcomes of neither OHC experienced individuals nor individuals with other types of CWC. The results of this study thus lend support to the disadvantage saturation perspective. Further studies are needed to explore this relationship.