Children with academic and behavioral difficulties have been found to report overly positive self-perceptions of performance in their areas of specific deficit. Researchers typically investigate self-perceptions in reference to both actual performance and ratings by teachers, peers, and parents. However, few studies have investigated whether or not adolescents with difficulty report overly positive self-perceptions. The present study sought to investigate self-perceptions of performance in the domains of spelling and math among a sample of adolescents with and without learning disabilities (LD). A total of 58 adolescents with and without LD participated. Adolescents with LD significantly overestimated their performance in math relative to their actual performance, but not in spelling, reflecting the predominant difficulty of the sample in the area of math rather than spelling. In addition, the magnitude of the gap between math predictions and actual performance was significantly greater for the group with LD than the group without LD. Findings support the existence of positive illusions in specific areas of deficit.