The current study explored coping and the relationship between coping, stressors, seriousness of delinquency, and internalizing and externalizing psychopathology in a sample of 93 (69 male, 24 female, M age=14.3 SD=1.4) court-involved adolescents. Participation took place in the Juvenile Court Clinics of Hampden, Hampshire, and Franklin Counties in Massachusetts. Participants completed the Brief COPE (Carver, 1997) with added items to measure aggressive coping, the Behavior Assessment System for Children Parent Report, Second Edition (BASC-2, PRS), and the Self-Report Delinquency Scale (SRD; Elliot, Huizinga, & Ageton, 1985). The documented history of delinquencies and stressors was collected from court records. An exploratory principal component analysis of the 14 subscales of the Brief COPE was conducted yielding 4 factors: approach coping, avoidant coping, seeking support, and emotional coping. Male participants reported more Active Coping than female participants whereas female participants demonstrated more Self-Blame Coping than male participants. Caucasian participants used more Acceptance, Venting, and Seeking Emotional Support than African-American and Hispanic participants. Participants with financial hardships reported using more Denial Coping than participants without financial hardship. Participants who were raised in single-parent households reported less Seeking Emotional Support Coping than participants who were raised in two-parent households. Participants who were subjected to parental physical abuse used less Seeking Instrumental Support Coping than participants without a history of parental physical abuse. Participants with a history of physical abuse between parents reported more Denial than participants without such history. Structural Equation Modeling (SEM) revealed that the avoidant coping factor was associated with more internalizing symptoms and that the approach coping factor was associated with fewer internalizing symptoms. Coping was not associated with externalizing symptoms or seriousness of delinquency. The current investigation provides preliminary evidence for the use of the Brief COPE scale in court-involved adolescents. Furthermore, the study introduced a novel way of capturing aggressive ways of coping that may be particularly relevant for delinquent populations. The differences in coping strategies as a function of stressor supports an argument that coping is flexible and is influenced by environmental circumstances. Implications of the results include the need to develop coping measures that capture unique dimensions of coping in court-involved adolescents and the need to develop coping-informed interventions for at-risk adolescents.