While listeners' metacognitive awareness of listening strategies has been reported to be a significant predictor of listening ability, factors that can moderate this predictive power have been taken for granted in the literature. The present study thus aimed at comparing the relationship between metacognitive awareness of listening strategies and listening proficiency among language learners with different levels of academic self-regulation (low, mid, and high). Three hundred and sixtynine high-school students participated in the study. To gather the data, Preliminary English Test, Metacognitive Awareness Listening Questionnaire, and Academic Self-Regulation Questionnaire were used. The findings of the study rejected the primary hypothesis that the degree of association between metacognitive awareness and listening comprehension is the strongest among highly self-regulated students. Further, regression analysis demonstrated that metacognitive awareness power value to predict listening proficiency, near to what is reported in the literature, was only gained when the mid self-regulated students were considered in the analysis.