Intelligent tutoring systems are efficient tools to automatically adapt the learning process to the student’s progress and needs. One of the possible adaptations is to apply an adaptive question sequencing system, which matches the difficulty of the questions to the student’s knowledge level. In this context, it is important to correctly classify the questions to be presented to students according to their difficulty level. Many systems have been developed for estimating the difficulty of questions. However the variety in the application environments makes difficult to apply the existing solutions directly to other applications. Therefore, a specific solution has been designed in order to determine the difficulty level of open questions in an automatic and objective way. This solution can be applied to activities with special temporal and running features, as the contests developed through QUESTOURnament, which is a tool integrated into the elearning platform Moodle. The proposed solution is a fuzzy expert system that uses a genetic algorithm in order to characterize each difficulty level. From the output of the algorithm, it defines the fuzzy rules that are used to classify the questions. Data registered from a competitive activity in a Telecommunications Engineering course have been used in order to validate the system against a group of experts. Results show that the system performs successfully. Therefore, it can be concluded that the system is able to do the questions classification labour in a competitive learning environment.