This project aimed to examine the associations between parental offending histories and offspring outcomes in early and middle childhood. Data were leveraged from the New South Wales Child Development Study (NSW-CDS), a large population-based study of 87,026 NSW children. The NSW-CDS is an intergenerational data linkage study combining information from cross-sectional surveys administered at age 5 and 11 years with administrative records. Data from Record Linkage 1 examined the association of parental offending with a range of early childhood (age 5 years) offspring outcomes (i.e., social competence; emotional maturity; language and cognitive development; communication and general knowledge; physical health and wellbeing; and, aggressive behaviour). Data from Record Linkage 2 examined parental offending and offspring conduct problems in middle childhood (age 11 years). Analyses revealed significant associations between parental offending and offspring vulnerabilities across a range of outcomes in early childhood and conduct problems in middle childhood. In early childhood, associations were greatest for cognitive outcomes. Violent and frequent offending had a greater magnitude of association compared to nonviolent and infrequent offending. Both maternal and paternal offending histories were associated with adverse offspring outcomes at both developmental periods. Prevention and intervention efforts should start at the earliest developmental periods, include mothers and fathers, and target both behavioural and cognitive problems in children.