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Juvenile delinquency and sexual risk taking behaviour commonly occur in conjunction. This places juvenile delinquents at significantly higher risk for early pregnancy and parenting than non-offending counterparts. However, less is known about how justice-involved adolescent parents and non-parents differ on offending-related outcomes. Using the Pathways to Desistance sample of 1,354 juvenile offenders, we compared adolescent fathers (n = 170) and adolescent mothers (n = 24) on a number of known risk factors for early pregnancy and offending-related outcomes. Our findings suggest that adolescent mothers and fathers are more likely to be older, present with significantly more psychosocial and demographic risk factors, and differ in their rates of aggressive and income-related offending compared to non-parents. Interestingly, offending patterns differed between adolescent mothers and fathers, which might suggest that early pregnancy operates as a moderator of offending risk in adolescence depending on gender. Because adolescent parenting was associated with more psychosocial and demographic risk factors, it also represents a key point for interventions which may alter and reduce offending. Given previously identified problematic long-term outcomes for children born to adolescents and justice-involved youth, identifying areas for intervention is critical.