This paper elaborates the concept of evaluation and self-assessment in the teaching of mathematics and other concepts important to explain the image on the realization winning learning. Also, the essential characteristic that influences this study is education. In a sample of 120 respondents, it was attempted to determine the significance of differences between evaluation and self-assessment in mathematics, in contrary the role of evaluation and self-evaluation in achieving winning learning in mathematics. Analytical - descriptive method and survey method were used in this study, which helped to confirm the hypotheses. The results were shown in tables and graphs and explained with the discussion. The whole operation was rounded with the conclusion.