Due to the COVID-19 pandemic, many Higher Education Institutions had to quickly shift from a traditional or blended approach to an online one and find solutions to foster students’ engagement and motivation. This paper aims to describe the pilot experience of an instructional methodology based on the combination of Gamification and Flipped Classroom, specifically designed to motivate, engage and support the students throughout a university course. The system was based on the use of several game elements (points, badges, role-playing, missions, boss fights, etc.), and was designed to evolve during the course according to the level of competence achieved by the students and their level of knowledge of the gamified system as well, so to keep them in the flow state. Preliminary results about students’ acceptance of this solution are provided and discussed.