Sexual risk taking among female delinquents represents a significant public health problem. Research is needed to understand the pathways leading to sexual risk taking among this population. This study sought to address this issue by identifying and testing two pathways from child maltreatment to non-condom use among 329 White and 484 African American female adolescent detainees: a relational pathway and a substance use coping pathway. The relational pathway indicated that child maltreatment would be related to non-condom use via depressive self-concept and condom use self-efficacy. The substance use coping pathway suggested that depressive self-concept and alcohol-based expectancies for sexual enhancement would mediate the relationship between child maltreatment and non-condom use. As hypothesized, the relational pathway variables were associated with one another in the expected directions; however, evidence of mediation was not found. Support for mediation was found for the substance use coping pathway. Exploratory across group comparison analysis indicated that the relational pathway was significant for White girls whereas the substance use coping pathway was significant for African American girls. Limitations and implications for future research are discussed.