This chapter provides a discussion on teaching and learning probability in the relationship between theoretical and empirical probability. We examine a small-scaled teaching experiment, which involves acts of experimentation. The purpose of the experiment is particularly on exploring and illustrating critical aspect of probability teaching, which involv es students’ concrete production and experimentation with data. Developing a background for the teaching experiment we proceed with reviewing previous research, which are highlighting issues on the relationship between empirical and theoretical probability in situations of experimentation.