Modern information and communication technologies allow to successfully use the methods of effectiveness measurement of various processes in particular in the field of education. From our perspective, success in the implementation of individual educational trajectories by university students requires the assessment model based on the use of modern information technology. In this article, we propose our own methodology for such measuring. It takes into account the entrant's competitive score and student's rating score. The user of the created system can choose the necessary information by criteria such as higher education degree, the form of study, department, and using the graph visualize the implementation of each student's educational trajectory. The presented methodology allows for evaluating objectively the quality of students` individual study plans and can be used in the development of universities rating and ranking criteria.