Nowadays it is important for companies to keep their profits and productivity high. This can be achieved by creating a good environment in which employees can perform at their best. Unfortunately, counterproductive work behavior (CWB) is widespread in the workplace and poses a serious threat to both organizational performance and employee well-being. Among the many potential risk factors for CWB, the Dark Triad (DT) personality traits (Machiavellianism, narcissism, and psychopathy) have received increasing attention in recent years. To assess the robustness and magnitude of the association between DT and CWB, we conducted a systematic review of the available literature on DT and CWB using the Preferred Reporting Items for Systematic Reviews and Meta-analysis (PRISMA) guidelines after a thorough search of several databases, 21 papers were included. The results showed that DT and CWB are positively associated. Psychopathy exhibited the strongest positive association with CWB, followed immediately by Machiavellianism and narcissism. Moreover, Machiavellianism and psychopathy showed positive correlations with both forms of CWB (organisational and interpersonal), whereas narcissism was positively correlated only with interpersonal CWB. Our findings highlight that even though organisations could benefit from people with DT at the performance level, there could be serious implications for well-being and an appropriate work environment due to CWB.