As decision-making research becomes more popular, the inclusion of personality traits has emerged as a focal point for an exhaustive analysis of human behaviour. In this study, we investigate the impact of psychopathic traits on cooperation in an iterated Prisoner’s Dilemma game with emotional facial feedback. Firstly, we observed how receiving a facial feedback after each decision affected players with different psychopathic trait scores, and how being informed about the opponent’s identity influenced cooperative behaviour. Secondly, we analysed the strategies adopted by each player, and how these choices were correlated with their psychopathic traits. Although our results showed no effect of different emotional content in the feedback on cooperation, we observed more cooperative behaviours in those players who were told their opponent was another fellow human, compared to those who were told it was a computer. Moreover, fearless dominance had a very small but consistent negative effect on overall cooperation and on the tendency to maintain cooperative behaviours. We also found that players’ personality scores affected the strategies they chose to play throughout the game. Hence, our experiment adds complexity to the body of work investigating psychopathic traits and social interactions, considering not only the environment of facial feedback but also the role of deception in experimental games.