Research examining the relationship between internalizing symptoms and antisocial behaviors has generally been cross-sectional in design. Thus, although extant data have substantiated a strong correlation between internalizing symptoms and antisocial behaviors, few studies have focused on describing the nature of the co-occurrence over time. This study examined the relation between growth in internalizing symptoms and longitudinal patterns of antisocial behavior in a sample of 283 inner-city males and their caregivers assessed as part of a longitudinal developmental risk study. Participants were assessed annually in four waves. Non-offenders and escalating offenders had lower levels of internalizing problems at wave 1 than did chronic minor and serious-chronic-violent offenders. Results revealed a developmental trend of decreasing internalizing problems across study years for most participants, as would be expected, with adolescents participating in serious, chronic, and violent patterns of antisocial behavior displaying greater internalizing problems than those participating in stable patterns of less serious or no antisocial behavior. Further, when there was escalation of seriousness and frequency of antisocial behavior, there also was increased internalizing problems relative to non-escalating juveniles. Results are discussed in the context of developmental psychopathology.