Self-regulation on behalf of the student is crucial in learning Mathematics through hypermedia applications and is an even greater challenge in these IT environments. Two aims are formulated. First, to analyze the effectiveness of a hypermedia tool in improving perceived knowledge of self-regulatory strategies and the perceived usage of the planning, executing and assessment strategy on behalf of students with low, medium and high levels of academic performance. Second, to analyze the effectiveness of the hypermedia tool in improving perceived usage of the strategy for planning, monitoring and evaluating on behalf of students with a perceived knowledge (low, medium and high). Participants were 624 students (aged 10–13), classified into a treatment group (TG; 391) and a comparative group (CG; 233). They completed a questionnaire on perceived knowledge (Perceived Knowledge of Self-Regulatory Strategies) and another one on perceived usage of the strategy for planning, performing and evaluating (Inventory of Self-regulatory Learning Processes). Univariate covariance analyses (ANCOVAs) and Student-t tests were used. ANCOVA results were not statistically significant. However, the linear contrast indicated a significant improvement in perceived knowledge of strategies among the TG with low, medium and high academic performance (p ≤ .001). Results are discussed in the light of past and future research.