Aims: Psychiatric symptoms, sleeping problems and stress are increasing in Swedish adolescents. The aim of this study was to test the hypothesis that a combination of two potential stressors (i.e., high academic proficiency and high urbanicity) in a school setting would be related to increased stress levels and stress-related symptoms among pupils. Our second aim was to evaluate correlations between perceived stress and psychiatric symptoms, sleep quality and personality traits. Methods: 202 Swedish high-school students from two schools, one with high academic proficiency in the Metropolitan Malmö area and one of average academic proficiency in a medium-sized town, participated. We used Internet-based versions of the following questionnaires: Symptoms Checklist 90 (SCL-90) for general psychiatric symptoms, Perceived Stress Scale (PSS-14) for stress, Pittsburgh Sleep Quality Index (PSQI) for sleep quality and Eysenck Personality Index (EPI) for personality traits. Results: There was no significant difference between the schools in any of the measured scales. Significant correlations between perceived stress and GSI score, PSQI score and the personality trait Neuroticism were observed. Conclusions: This study suggests no difference between the high academic proficiency/metropolitan school and the average academic proficiency/medium-sized town school in perceived stress levels or stress-related psychiatric symptoms.