ObjectiveTo investigate the association between history of academic failure (HAF) and self‐reported depression, anxiety, and stress among undergraduate dental students.MethodsThis study involved 244 dental students from one university. An online questionnaire collected information on the following variables: socioeconomic status, behavior, use of licit/illicit drugs, and the choice of dentistry as an undergraduate field of study. The 21‐item Depression Anxiety Stress Scale (DASS‐21) was applied. HAF in at least one subject during a participant's undergraduate tenure was defined as the main outcome. Bivariate and multivariate analyses were performed using Poisson regression with robust variance. In addition, a subgroup analysis was performed for the variable “dentistry as the first choice for undergraduate studies.”ResultsThe prevalence of HAF was 25.00% (n = 61). Among those students, the mean number of academic failures was 5.41 ± 6.38 (range: 1–33). Higher rates of HAF were observed among older and non‐white dental students. Moreover, those who self‐reported at least severe depression presented a 79% higher HAF prevalence ratio (PR) (95% confidence interval [95% CI]: 1.15–2.80). Similar findings were detected among those who reported (PR: 1.79; 95% CI: 1.06–4.46) or did not report (PR: 2.21; 95% CI: 1.10–4.46) interest in dentistry as a first undergraduate option. Conversely, among women and students who did not choose dentistry as their first option, HAF was significantly lower (PR: 0.41; 95% CI: 0.21–0.80).ConclusionHigher HAF rates are observed in students who are older, non‐white, and self‐report at least severe depression. However, dentistry as a first option for undergraduate studies was not associated with HAF.