Background: Persons with Obsessive Compulsive Disorder and individuals in conflict with law are prone to experience guilt and regret which can have significant implications on their lives. Guilt and regret are two very prominent emotions found in individuals with Obsessive Compulsive Disorder A question then arises whether the individuals who are in Conflict with Law experiences the same kind of guilt and regret, which is experienced by the persons suffering from obsessive compulsive disorder; another aspect that too seeks attention is how related is the coping strategy of the two distinguished population. Methods: The objective of this study was to aim assess and compare the guilt, regret and coping in individuals with obsessive compulsive disorder and individuals in conflict with law. The sample size consists 60 individuals (18-55years of age), of whom 30 individuals were with OCD taking treatment in the Institute of Psychiatry and 30 individuals in conflict with law, who were taken from the Presidency Correctional Home and Alipore Women Correctional Home. Participants were selected purposively. The Revised Mosher Guilt Inventory, Regret Scale and Brief Cope were administered of the participants of either group for the assessment guilt, regret and coping respectively. Data analysis was done by the SPSS-25 (Windows version). Descriptive statistics, independent samples t test and chi-square test were used. Results: In OCD group, majority of the participants were found to have higher educational qualifications, e.g. intermediate, graduation or more, whereas, in persons in conflict with law group, most of them were either illiterate or minimally educated, nearly equal participation of males and females was observed in either group, mean ages were 32.93±9.21 and 40.00±8.38 in OCD and persons in conflict with law groups respectively. No significant differences were noted between these two groups in coping and regret. In case of guilt, significant difference was noted in 'guilty conscience', where OCD patients reported significantly higher scores than that of persons in conflict with law. In other two forms of guilt, i.e., sexual guilt and hostility guilt no significant differences were noted. Conclusion: Difference in guilt between OCD patients' and the persons' in conflict with might be due to several reasons, ranging from core illness related factors to larger socio-cultural factors. Roles of personality might as well have some association with it. Giving conclusive remark about guilt, regret and coping about these two divergent populations might not be possible with this small size. In future, studies should be carried out on larger samples which should be selected through stratified sampling method for securing more accurate information about those issues. Factors like, family structure and functions, marital relationship, family support and personality disposition should also be studied.