In February 2022, the Free University of Bolzano, in cooperation with NOI Techpark of Bolzano, offered an extra-curricular entrepreneurial programme named “Students & Company Sprint”. It was a five-day event where three companies presented an innovation challenge that student teams had to solve, mentored by experts and scientists. The student teams included second- or third-year bachelor students and master students from faculties of the Free University of Bolzano. The event followed the methodology of Google Design Sprint and was oriented towards problem-based learning in a limited time. After the Sprint, an online survey was sent to the students with questions based on the competences of the European Entrepreneurship Competence framework, revealing that overall the Sprint had a very positive effect on students’ entrepreneurial competences. The largest effect was on the ability to “work with others”. The University concludes that the type, complexity, and wording of the challenge determines the students’ learning of entrepreneurial competences. Moreover, such a challenge should be sufficiently simple and open to leave room for creativity.