Few studies have assessed multiple stress factors as a potential risk for menstrual disorders. This study evaluated whether work-related stress or life event stress was associated with alterations in menstrual function of military personnel. The study is unique in that it evaluated the association between race and three job factors—job stress, handling chemical mixtures, and being a military or civilian employee of the US Air Force. A comprehensive questionnaire was administered to 170 healthy, premenopausal employed women to examine the relationship between work-related or life event stress and menstrual disorders. Multiple logistic regression analyses showed no statistically significant association between work-related stress and menstrual disorders, whereas life event stress was significantly associated with dysmenorrhea (odds ratio [OR], 2.20; 95% confidence interval [CI], 1.08 to 4.50) abnormal cycle length (OR, 3.42; CI, 1.12 to 10.50), and hypermenorrhea (OR, 2.99; 95% CI, 1.20 to 7.42). Having one or more menstrual disorders was significantly associated with life events by race interaction (OR, 6.52; 95% CI, 2.45 to 17.36). Non-Caucasians had significantly increased risks of hypermenorrhea (OR, 4.99; 95% CI, 2.07 to 12.05) and abnormal cycle length (OR, 4.12; 95% CI, 1.47 to 11.55). The prevalence of menstrual disorders in this military population was 31.2% for dysmenorrhea, 17.9% for hypermenorrhea, and 12.0% for abnormal cycle length. This study suggests that women in the military report less day-to-day job stress but more atypical life events, including those related to their jobs, and that these life events are associated with adverse menstrual consequences.