Positive illusions are systematically inflated self-perceptions of competence, and are frequently seen in areas of great difficulty. Although these illusions have been extensively documented in children and adults, their role in typical adolescent emotion regulation is unclear. This study investigated the relationship between positive illusions, depressive symptomatology, and school stress in a sample of 71 school-based adolescents. Findings revealed that adolescents who were achieving slightly below average in math significantly overestimated their performance, but adolescents did not overestimate their performance in spelling. Positive illusions in math were negatively related to depressive symptomatology. Implications for positive illusions theory are discussed.