Given prevalence rates and negative consequences that adolescents’ perpetration of dating violence may have on an individual’s well-being and future relationships, it is imperative to explore factors that may increase or reduce its occurrence. Thus, we aimed to identify how multiple contextual risk factors (individual, family, schools, and neighborhoods) were related to adolescents’ perpetration of dating violence over a 6 year period. Then, we assessed how neighborhood collective efficacy, an important predictor of urban youths’ well-being, buffered the relationship between each of the risk factors and adolescents’ perpetration of dating violence. Three waves of data from the Welfare, Children, and Families: A Three-City Study were used (N = 765; Ages 16–20 at Wave 3). The sample is 53 % female, 42 % African-American, and 53 % Hispanic. For the total sample, drug and alcohol use, low parental monitoring, academic difficulties, and involvement with antisocial peers were significant early risk factors for perpetration of dating violence in late adolescence. Risk factors also varied by adolescents’ race and sex. Finally, perceived neighborhood collective efficacy buffered the relationship between early academic difficulties and later perpetration of dating violence for Hispanic males. These results imply that multiple systems should be addressed in dating violence prevention programs.