Parent–child acculturation discrepancy has been considered a risk factor for child maladjustment. The current study examined parent–child acculturation discrepancy as an ongoing risk factor for delinquency, through the mediating pathway of parental knowledge of the child’s daily experiences relating to contact with deviant peers. Participants were drawn from a longitudinal project with 4 years between data collection waves: 201 Chinese immigrant families participated at Wave 1 (123 girls and 78 boys) and 183 families (110 girls and 73 boys) participated at Wave 2. Based on the absolute difference in acculturation levels (tested separately for Chinese and American orientations) between adolescents and parents, one parent in each family was assigned to the “more discrepant” group of parent–child dyads, and the other parent was assigned to the “less discrepant” group of parent–child dyads. To explore possible within-family variations, the mediating pathways were tested separately among the more and less discrepant groups. Structural equation modeling showed that the proposed mediating pathways were significant only among the more discrepant parent–adolescent dyads in American orientation. Among these dyads, a high level of parent–child acculturation discrepancy is related to adolescent perceptions of less parental knowledge, which is related to adolescents having more contact with deviant peers, which in turn leads to more adolescent delinquency. This mediating pathway is significant concurrently, within early and middle adolescence, and longitudinally, from early to middle adolescence. These findings illuminate some of the dynamics in the more culturally discrepant parent–child dyad in a family and highlight the importance of examining parent–child acculturation discrepancy within family systems.