A number of studies have investigated the association between psychiatric disorders and alterations in cognitive development, academic performance, and learning ability. However, few studies have explored the relationship between stressful events and grade repetition. Therefore, the main goal of the present study was to compare the frequency of exposure to stressful events, academic performance, executive functioning, and performance on working memory tasks between adolescents with and without a history of grade repetition. This was a cross-sectional study. The sample was composed of 83 adolescents divided into two groups: (1) individuals with a history of grade repetition (n = 39) and (2) participants who had never repeated a grade (n = 44). Participants were administered tests to assess executive functions, intelligence, exposure to stressful events, and academic performance. Results showed that individuals with a history of grade repetition reported to experiencing a higher number of stressful events in adolescence, had worse academic performance, and obtained lower scores on executive functioning and working memory tasks than non-repeaters.