Purpose: Although parental criminal offending is a recognized risk factor for conduct problems among offspring, its impact on the continuity and discontinuity of children’s behavioural and emotional difficulties during the early development is less well known. We used data from a large, population-based record-linkage project to examine the relationship between parental offending and the continuity and discontinuity of children’s conduct, attentional, and emotional difficulties from early to middle childhood while also considering the role of timing of the parental offending exposure. Method: Data for 19,208 children and their parents were drawn from the New South Wales Child Development Study. Multinomial regression analyses tested associations between mother’s and father’s history and timing of any and violent offending, and patterns of continuity or discontinuity in offspring emotional, conduct, and attentional difficulties between ages 5 and 11 years. Results: Maternal and paternal offending each conferred a significantly increased risk of all the patterns of developmental difficulties, including those limited to age 5 only (remitting problems), to age 11 only (incident problems), and to difficulties present at both ages 5 and 11 years (persisting problems). Greatest odds were observed for persisting conduct problems. Paternal offending that continued through early and middle childhood had the greatest association with child difficulties, while the timing of maternal offending had a less prominent effect on child developmental difficulties. Conclusion: Parental offending is a strong risk factor for early and pervasive behavioural and emotional problems in offspring, and may be a key indicator of high risk for later antisocial behaviour.