The purpose of this study is to design a personalized adaptive and intelligent web based tutoring system based on learning style and expert system named UZWEBMAT and to evaluate its effects on 10th grade students’ learning of the unit of probability. In the study, initially, learning objects were prepared in three different ways in relation to three sub-learning areas of Visual–Auditory–Kinesthetic (VAK) learning style for each subject of the probability unit. These were appropriate for secondary school mathematics curricula. Then, they were transferred into the digital environment. Each student’s dominant learning style determines the content to which s/he will be directed since s/he is directed to the content that is appropriate for his/her learning style. The course to be followed by the students within UZWEBMAT and their browsing around the pages are decided by expert system integrated into the system. This expert system sets the situations in which s/he will get solution supports and the course s/he will follow in accordance with the performance of the student. Hereby, each student may follow a different course, and the solution supports s/he will get may also differ highlighting the individual learning. The sample of the study consists of 81 10th grade students and 3 mathematics teachers from two high schools in Trabzon, Turkey. Qualitative data were obtained both from the teachers and students participating in the study in order to answer the research questions about the implementation and evaluation of UZWEBMAT for mathematics teaching in a high school classroom. Obtained data were analyzed using qualitative data analysis methods. According to the results of the present study, positive opinions of students and teachers such as taking into account the individual learning differences and deriving mathematical relations and formulas through exploration became prominent. In addition, there were also other positive opinions of students and teachers such as providing permanent learning and introducing learning responsibility to the students. In this sense, it was concluded that UZWEBMAT is a beneficial instrument for both students and teachers.