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To explore the association between previous severe HIV disease, defined as past Centers for Disease Control and Prevention class C diagnosis, and neurocognitive and psychiatric outcomes in long-term survivors of perinatally acquired HIV.A retrospective cohort study of perinatally HIV-infected adolescents receiving outpatient care at a single site.Comparisons were made between those with and without class C diagnoses.Eighty-one patients formed the study group, 47% were females and 72% were African–American. Median patient age was 15 years (interquartile range 13–17). Of the study group, 47% had a past class C diagnosis. The median age at class C diagnosis was 3.1 years (interquartile range 0.9–8.1). There were no significant differences between the groups with respect to most recent CD4+ cell percentage or plasma viral RNA level. Class C patients were more likely to have a history of psychiatric diagnosis [odds ratio 2.6; 95% confidence interval (CI) 1.1–6.3], psychiatric hospitalization (odds ratio 4.8; 95% CI 1.2–17.4), or learning disability (odds ratio 4.5; 95% CI 1.7–11.4). There was a significant difference in full-scale intelligence quotient between the groups (adjusted linear regression coefficient −11.7; 95% CI −17.9 to 5.5). After adjusting for age at antiretroviral therapy initiation, the associations between class C diagnosis and lower full-scale intelligence quotient, learning disorders, and psychiatric diagnoses remained significant.A distant history of AIDS diagnosis was associated with an increased risk of neurocognitive and psychiatric impairment in adolescents with perinatally acquired HIV. Further research should help delineate if early treatment, possibly soon after birth and definitely prior to AIDS diagnosis, might lead to improved outcomes.