The Undergraduate Course in Obstetrics and Gynecology at the Catholic University in Paraná State, Brazil, is based on problem-based learning. The program analyzes various clinical cases to form the course content. For each clinical case, the professors define the primary patient work-up protocol and the corresponding clinical/diagnostic techniques, in order to establish the set of measures or procedures that students are expected to perform. In order to include information and communication technologies in the students' learning process, developed a system that allows the students to follow a step-by-step approach to these measures and procedures. The overall objective of the current article was to design a mathematical and computational model that allows obtaining indices of similarity between the patient work-up approaches defined by the professors and those actually performed by students.