Japanese teachers are mentally and physically burdened with various work stressors. This cross-sectional study examined the relationship between depressive symptoms and perceived individual level occupational stress including role problems among Japanese schoolteachers. This study included 1,006 teachers working in public schools in a Japanese city. The Japanese version of Zung’s Self-Rating Depression Scale (SDS) was used to evaluate depressive symptoms, and the Generic Job Stress Questionnaire was used to evaluate occupational stress and three measures of social support. Subjects with SDS scores of more than 50 were categorized into the “depressive group.” We examined the relationship between depressive symptoms and perceived individual level occupational stress using multiple logistic regression analyses. A total of 202 (20.1%) teachers belonged to the depressive group. We found that high role ambiguity, high role conflict, high quantitative workload, and low social support from family or friends were significantly related to depressive symptoms. To moderate role ambiguity and role conflict experienced by teachers, it is necessary to clarify the priority order of teachers’ work. Furthermore, it is necessary to reduce workload by focusing on the content of teachers’ work and the setting of education itself. Focusing on these elements will reduce teachers’ depressive symptoms.