University lecturers have been encouraged to adopt innovative methodologies and teaching tools in order to implement an interactive and appealing educational environment. The MathE platform was created with the main goal of providing students and teachers with a new perspective on mathematical teaching and learning in a dynamic and appealing way, relying on digital interactive technologies that enable customized study. The MathE platform has been online since 2019, having since been used by many students and professors around the world. However, the necessity for some improvements on the platform has been identified, in order to make it more interactive and able to meet the needs of students in a customized way. Based on previous studies, it is known that one of the urgent needs is the reorganization of the available resources into more than two levels (basic and advanced), as it currently is. Thus, this paper investigates, through the application of two clustering methodologies, the optimal number of levels of difficulty to reorganize the resources in the MathE platform. Hierarchical Clustering and three Bio-inspired Automatic Clustering Algorithms were applied to the database, which is composed of questions answered by the students on the platform. The results of both methodologies point out six as the optimal number of levels of difficulty to group the resources offered by the platform.