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The use of self-regulation skills among learners is of utmost importance for their academic achievement and learning success. Even if these skills do not get specific attention at school, it could be assumed that they develop with general learning experience and age. This cross-sectional study intends to determine the developmental trends of self-regulation skills and academic motivation among adolescents in relation to gender and age. A sample of 2,349 Estonian students aged eleven to nineteen completed an online MSLQ questionnaire adapted for schoolchildren. The age and gender-specific comparison revealed interesting, albeit somewhat unexpected trends in motivation and strategy use among adolescents.