Creating contexts in teaching, learning, and assessing the student involves a complex activity whose purpose is the student's progress. The connection between the three processes can be assured by choosing the best educational context for the university teacher. In the student-centered university educational process, having the students as partners in the teaching process and assessing them based on contextual learning is essential. This study analyses the influence of assessment based on contextual learning on students' learning results and used descriptive and comparative quantitative research with a non-experimental design to achieve this goal. The sample was 114 students from the Teacher Training Department, West University of Timisoara, Romania, second year of study, Level 1 of the Postgraduate Program, for the academic year 2021–2022 (20 males and 94 females). Using two formative context-based assessment tasks and one summative content-based assessment task, the study revealed that assessments based on practical contextual learning tasks positively impact students' results more than content-based assessments. Also, the contextual assessment task type influences students' results, with the practical context determining better results than a cognitive-theoretical context. The study's limitations suggested that many factors could be involved in studying the impact of different types of contextual assessment on students' results. Future experimental research could be done on considering experimentally confirmed variables and criteria for construing and choosing the appropriate type of task for formative and summative contextual assessment that confirms students' progress, including new technologies support in contextual assessment.