The purpose of the three papers included in this dissertation is to examine the relationship between criminal justice involvement and sexual HIV risk for drug abusing men and their primary female sexual partners. The sample of interest comes from a longitudinal epidemiological study funded by the National Institute on Drug Abuse involving a random sample of 356 men on methadone. Paper 1 examines whether a relationship exists between criminal justice involvement and HIV risk and prevalence beyond the role of drug abuse. Paper 2 utilizes a longitudinal design and propensity score matching methodology to explore whether recent criminal justice involvement is associated with increased likelihood of subsequent HIV risk behaviors among men on methadone. Finally, the third paper focuses on primary heterosexual relationships and examines how couple-level incarceration history is associated with HIV risk between partners and for each partner separately. The three papers demonstrate a significant and temporal relationship between criminal justice involvement and sexual HIV risk, as well as numerous individual and couple-level variables which may act as contributing risk or protective factors. The findings from this dissertation provide insight into the context of sexual HIV risk for drug abusing offenders and their sexual partners which is critical to informing and improving HIV prevention interventions for this vulnerable population.