In teaching of mathematics, with a special emphasis on the area of probability, it is important for all students to be able to come up with numerous conclusions independently, with the help of their own preknowledge. Furthermore, students should, as much as possible, be involved in the learning process which enables them to combine mathematical theory with examples from the real life. This paper presents the historical context of probability development, as well as psychological barriers and misunderstandings affecting students’ understanding of probability notions and concepts in order to approach the learning of probability in the right way. Passing through a variety of topics in probability, a rigorous mathematical background is compared to the methodical approach in the secondary school and supported by activities in which students use inquiry methods to adopt new teaching content. Moreover, the importance of creating links between mathematical and intuitive concepts is also emphasized. Different approaches to the probability contents are presented, as well as the ways in which the data is being read with the significant role of technology. Of course, every approach must be moderate and a teacher needs to find the right measure. This can best be done by the observing the needs of students themselves.