The study reported in this paper concerns the tensions and conflicts that teachers experience while they enact a new set of reform-oriented curricular materials into their classrooms. Our focus is οn the interactions developed in two groups of teachers in two schools for a period of a school year. We use Activity Theory to study emerging contradictions and we elaborate on the construct of dialectical opposition to understand the nature of these contradictions and their potential for teacher learning. We provide evidence that discussions about contradictions and their dialectical character in the two groups support teachers to engage differently in mathematics teaching and learning and carry potentials for shifts in the practices that evolve in their classrooms. Our study addresses empirically in the context of mathematics teaching the philosophical claim about the role of contradictions as a driving force for any dynamic system.