The current study explored the intergenerational transmission of aggression and antisocial behavior by examining mothers' juvenile delinquency, their pregnancies, and its impact on their children's aggressive behavior. The sample consisted of the first 181 biological mothers recruited as part of the Vancouver Longitudinal Study on the Psychosocial Development of Children (British Columbia, Canada). Results indicated that mothers who were juvenile delinquents were more likely to experience social adversity, to use substances during pregnancy and to offend in adulthood. Furthermore, mothers who reported juvenile delinquency had children who were more physically aggressive and had an earlier onset of physical aggression. This pattern of association held when controlling for sociodemographics, social adversities, prenatal substance exposure, and criminal involvement in adulthood. The study findings highlighted the importance of understanding the role and impact of female delinquency and motherhood on the intergenerational transmission of antisocial behavior. Copyright © 2012 John Wiley & Sons, Ltd.