Although multiple domains of risk are theorized to predict adolescent delinquency, father-specific risk in the context of other risks is under-researched. Using the low-income Future of Families and Child Wellbeing cohort (48% Black, 27% Hispanic, 21% White, 51% boy, N = 4,255), the current study addressed three research questions. (1) are father-, mother-, child-, and family-level cumulative risk during early childhood associated with adolescent delinquent behavior?, (2) does child self-control in middle childhood mediate the associations between fathers’ and mothers’ cumulative risk and adolescent delinquent behavior, and do quality of parent’s relationships with children and parental monitoring in middle childhood mediate the association between child cumulative risk and delinquent behavior?, (3) do parenting, quality of parent-child relationships in middle childhood, and child sex at birth moderate the associations among fathers’, mothers’, children’s, and family risk and adolescent delinquent behavior? Results indicated father, child, and mother risk at ages 3–5 were significantly and positively associated with youth-reported delinquent behavior. Higher levels of family risk were associated with less delinquency when 9-year-olds felt closer to fathers than when they felt less close. Children’s self-control at age 9 mediated the associations between father and child risk and delinquent behavior.