Using latent class analysis (LCA), this study identified a dyadic taxonomy of delinquent youth categorized by varying types of maternal-youth reporting discrepancies (i.e., youth < maternal, youth > maternal) within a sample of 764 14-year-old high-risk youth. Four distinctive subgroups of youth were identified, two of which reported more than a minimal degree of informant discrepancy across all domains of delinquent behavior. One subgroup exhibited higher maternal-reported delinquency in comparison with youth reports, and one subgroup exhibited higher youth-reported delinquency in comparison with maternal reports. Additionally, risk factors (e.g., peer delinquency, caregiver monitoring) and delinquency-related difficulties (e.g., police contact) were associated with youth placement in the LCA-identified subgroups. Study findings suggest that youth with higher levels of self-reported delinquency compared with maternal reports may be at greater risk for delinquency-related difficulties due to problems related to inadequate monitoring by caregivers combined with greater involvement with peer delinquency.