The aim of this study was to examine the relationship between menses-associated health problems of women, such as premenstrual symptoms, menstrual pain and irregular menstrual cycles, and psychosocial stress. A cross-sectional study was conducted among Japanese college students, measuring psychosocial stress levels by means of IMPS (The Inventory to Measure Psychosocial Stress). A total of 264 female students (mean age 19.4 years), who were invited to participate in the study in October 2007, completed the questionnaire, which dealt with anthropometric data, lifestyle, menstrual history, and menstrual health status. Forty-three students were excluded due to missing data, and the remaining 221 were analyzed. The proportions of students who reported premenstrual symptoms, menstrual pain, and the experience of irregular menstrual cycles were 79%, 79%, and 63%, respectively. Students who reported premenstrual symptoms, menstrual pain, and the experience of irregular menstrual cycles had higher stress scores than those who did not. Multiple logistic regression analyses were used to identify independent factors associated with having premenstrual symptoms, menstrual pain, and the experience of irregular menstrual cycles. Stress score, heavy menstrual flow, and menstrual pain were significant predictors for premenstrual symptoms, while age at menarche and having premenstrual symptoms were significant predictors for menstrual pain. Both stress score and body mass index were found to be significant predictors for having experienced irregular menstrual cycles. The results suggest that psychosocial stress is independently associated with premenstrual symptoms and the experience of irregular menstrual cycles among college students, implying that changes in the functional potentiality of women as a result of stress are related with changes in their menstrual function.