In this paper, we consider grading within a dilemmatic space in which teachers have to negotiate often competing policies, tools, consequences, contextual and social conditions, and assessment theories for decision-making. While previous research into grading has focused primarily on the reliability and composition of teachers’ grades as well as the predictive and concurrent validity of grades, our research explores the ways teachers negotiate grades within a dilemmatic space. Specifically, the purpose of this study is to examine teachers’ negotiated responses to classroom grading dilemmas. Data were collected from Canadian and Swiss secondary teachers through qualitative methods: interviews, focus groups, and writing reflections. Through inductive thematic analysis, results identified five themes that emerged from the articulation of grading dilemmas which collective characterize the dilemmatic space for teacher grading: (a) fairness, (b) justification of grading decisions and communication, (b) teacher investment, (d) commitments to learning, and (e) validity of grading systems for learning system. Collectively, these results hold implications for teacher assessment education and grading theory, specifically the consideration of grading as a cross-cultural phenomenon and grading as a dilemmatic space.