Mathematical education in Greece is constantly evolving in the pursuit of optimal learning outcomes for students despite their cognitive differences. This study seeks to gain insight into the use of new technologies in teaching probability theory and the gender differences in the comprehension of probability theory. To this end, a survey was conducted involving 500 students of the Department of Statistics and Insurance Science at the University of Piraeus. The respective questionnaire involves questions of self-reported results and employs the Likert scale to obtain the students' perceptions. Our data demonstrate no difference among the genders regarding the use of new technologies or their performance (i.e., the test scores) in the relevant courses.