Purpose: This study describes the lifetime prevalence of teen dating violence (TDV) perpetration in a sample of middle school students from high-risk urban communities and examines the relation between TDV and related cognitive and behavioral risk factors. Methods: Surveys were administered to 2,895 middle school students in four U.S. cities; 1,673 students (58%) reported having dated and were included in analyses. The sample was 52.3% female, 48.2% non-Hispanic black/African-American, 38.2% Hispanic, 4.8% non-Hispanic white, and 7.6% other race. Six types of TDV perpetration were assessed: threatening behaviors, verbal/emotional abuse, relational abuse, physical abuse, sexual abuse, and stalking. Results: Of the students who had dated, 77% reported perpetrating verbal/emotional abuse, 32% reported perpetrating physical abuse, 20% reported threatening a partner, 15% reported perpetrating sexual abuse, 13% reported perpetrating relational abuse, and 6% reported stalking. Girls were more likely than boys to report perpetrating threatening behaviors, verbal/emotional abuse, and physical abuse, and boys were more likely to report perpetrating sexual abuse. Involvement in bullying positively predicted perpetration of TDV, albeit, in different ways for boys and girls. Other risk factors differed by sex. For instance, alcohol use and sex initiation predicted multiple forms of TDV perpetration for boys, whereas weapon carrying and emotional symptoms predicted several forms of TDV perpetration for girls. Conclusions: The prevalence of TDV was high in our sample. Important sex differences in rates of perpetration and risk factors emerged. Comprehensive prevention programs that target TDV and related risk factors, such as bullying and other risk factors, seem warranted.