There is a growing trend among European Universities to show interest towards the dual career of student-athletes and related issues. Nowadays, the European Union is committed to promote and implement, through specific funding programs, research projects aimed to identify and build new tutoring models for student-athletes who follow their courses. Taking inspiration from Systems Theory, we can affirm that the dual-career of student-athletes is greater than the sum of its parts. Tutoring is a part of the system and forms a subsystem in itself. For this reason, it is always necessary to couple theory and practice, research and evaluation integrating them into a flexible and adaptable system in order to build and develop an effective tutorship program for student-athletes. This paper will show the importance of developing tutoring and mentoring programs addressed to student-athletes and focused on flexible learning models (Agile Learning, Community of Learning, and Reflective Practitioner’s critical thinking) which adopt and incorporate new Web 2.0 communication technologies and tools. In addition, a case study and its results will show the genesis of a specific tutorship pedagogical model (DU.C.A.S.T.UN ) addressed to student and post-career athletes developed and implemented at the University of Rome Foro Italico, Italy, within the Erasmus+ Project named ESTPORT. In conclusion, our paper will stress the effectiveness of the model implemented and the possibility of its reuse in other universities or contexts.