Applying both latent variable and network frameworks, we conducted a comprehensive psychometric evaluation of the diverse array of symptoms from three externalizing dimensions, including attention problems, aggressive behavior, and delinquency/rule-breaking of the Child Behavior Checklist (Achenbach, 1991) across six time points from childhood to early adolescence. We also examined sex differences. Participants (N = 1,339) were drawn from two multisite longitudinal studies: Fast Track and the Child Development Project. Parents reported on externalizing psychopathology in kindergarten and Grades 1, 2, 4, 5, and 7. Using exploratory structural equation modeling, we found almost uniformly excellent fit across time and samples. However, we also observed multiple cross-loadings and heterogeneity in terms of which symptoms cross-loaded across time points. Alternatively, using network modeling, we observed that symptoms of attention problems and aggressive behavior had stronger connections, relative to delinquency/rule-breaking, across time and samples. Significant differences in overall connectivity were found at early (kindergarten vs. Grade 1, Grade 1 vs. Grade 2) and late (Grade 5 vs. Grade 7) time points for the combined sample and only late time points for the male sample. In addition, the items impulsive and lies or cheats consistently displayed the greatest bridge strength, that is, symptom from one dimension that connects to symptoms from another dimension, across time and samples. Our results illustrate how two methods—latent variable and network modeling—provide important and complementary information on multidimensional constructs. Findings also inform understanding of externalizing psychopathology through childhood to early adolescence by identifying key symptoms, critical transition points, and possible transdiagnostic liabilities.