This study examines the effects of matching and mismatching on web-based learning with a human-centered approach. In particular, we emphasize on how prior knowledge and gender differences affect students' reactions to a matching/mismatching environment. In general, the results demonstrate that learners in a matching condition perform better than those in a mismatching condition. Furthermore, males can overcome the mismatching condition when they acquire declarative knowledge. In contrast, females can positively face the mismatching condition when they obtain procedural knowledge. In summary, the matching/mismatching is not only related to gender differences but also is linked to declarative/procedural knowledge.