Combining individual group work assessment with expectations of collaboration and shared learning can be seen as a paradox. In this chapter we explore and problematise whether it is possible to combine cooperative learning, an approach that has great potential to contribute to joint knowledge development between students, with teacher’s curricula knowledge requirements to assess student knowledge and abilities individually. The latter can create competition between the students. We propose adding a further dimension of contemporary global perspectives on cooperative learning in education by increasing knowledge about what happens in the meeting between cooperative learning and individual group work assessment. We will address some salient possibilities and challenges regarding individual group work assessment based on theory and research, but primarily we will discuss results from our group work assessment intervention project. We will also contribute by noting some practical implications presented as recommendations for teachers who employ the assessment practice when using cooperative learning.