In this preregistered study, we studied the extent to which family functioning and family regularity compensated for (compensatory model of resilience, Garmezy et al., Child Development 55:97–111, 1984) and buffered against (risk-protective factor model of resilience, Fergus and Zimmerman, Annual Review of Public Health 26:399–419, 2005) the influence of cumulative risks (CRs) on young children’s internalizing and externalizing problems. We conducted path analyses on multi-informant, longitudinal data from 3159 families enrolled in the Generation R Study, a large prospective birth cohort in the Netherlands. Children self-reported on internalizing and externalizing problems at age six. Mothers and fathers reported on 48 CRs between birth and child age five. Mothers reported on family regularity items at child ages two and four, and on family functioning at child age four. CR was positively associated with girls’ and boys’ internalizing problems, and with boys’ externalizing problems. We did not find support for a compensatory or buffering role of family functioning on the association between CR and children’s internalizing or externalizing problems. Our findings suggest that the use of a CR index may be beneficial for identifying children who are at higher risk for developing internalizing and externalizing problems in the early school years, as well as for planning treatment and intervention. Keywords: Cumulative risk, Internalizing problems, Externalizing problems, Family functioning, Family regularity, Early childhood.