Negotiations in real life are generally perceived as distributive tasks that produce winners and losers. Nevertheless, in almost all cases there is an opportunity to expand the joint outcome through cooperation; reaching a win-win agreement. The aforementioned characteristic of the negotiation task is similar with what is observed in a social dilemma, situations where individual self-interesting behaviour leads to inferior collective results. Therefore, elements from both phenomena can be used in order to advance the state of art on how to achieve win-win agreements in Labour-Management disputes. An important factor that can be seen as a necessary condition in order to achieve cooperation between parties is the existence of some level of trust. By adopting a deductive approach, a number of variables which influence negotiations between labour and management were isolated. These variables served as the elements for constructing a proposed theory that through a Decision Support System (DSS) will facilitate integrative agreements by fostering trust between the negotiators. In order to test the validity of the proposed theory, two research questions have been addressed aiming to verify; a) the set of variables used in the proposed theory and b) the facilitation of integrative agreements through fostering trust. The proposed research questions were tested through: i) a survey that was distributed in three countries, ii) a numerical experimentation with all possible outcomes and iii) by a set of interviews that aimed to provide deeper insight in the problems under examination. The results from the survey questionnaire and the information elicited by interviewing experts worked as confirmatory evidence in order to verify the validity of the set of variables. The numerical experimentation, combined with statements by the experts that participated in the interviews revealed confirmatory evidence for the ability of the proposed theory to foster trust and, thus, facilitate integrative results.