The main purpose of this study is to measure listening comprehension skills of 5th grade school students with the help of web based system. This study was conducted on 5th grade students studying at the primary schools of Eskisehir. The scale used in the process of the study is "Web Based Listening Scale". In the process of the study, the level of differentiation listening skill and educational level of mother and father, family income level, Turkish Course grading note and the most popular and listened music genre were investigated. According to the obtained results significant difference was found with listening skills and educational level of mother and father, family income level and the most popular and listened music genre. Also it was found that there is a powerful relationship between listening skills and Turkish Course grading note. In the process of the research, it was observed that the students used the web based system are more attentive and motivated. Nevertheless, personalized measuring environment was provided by the web based system. Finally, it can be said that the web based systems can be used positively for language learning, teaching, and instruction, improving, measuring and assessing process.