Aims: To evaluate whether serum estrogen level is associated with chronic pain, masticatory dysfunction, and depressive symptoms and/or somatization in women with temporomandibular disorders (TMD) and different menstrual cycle status. Methods: A total of 64 women were allocated into one of three groups: one composed of women with normal menstrual cycles (Group 1), one composed of pregnant women (Group 2), and one composed of women in surgical menopause (Group 3). All respondents underwent a standardized clinical examination with the Research Diagnostic Criteria for TMD (RDC/TMD). Diagnoses were generated according to Axis I, and grades of chronic pain, depressive symptoms, and somatization were evaluated according to Axis II. The level of serum estradiol was measured by using the immunofluorescent method. Analysis of variance, Kruskal-Wallis test with post hoc comparisons via series of Mann-Whitney U tests, and Spearman correlation coefficient were used for comparisons between study participants. Results: Reported pain was decreased with the progress of pregnancy among the women from Group 2 and was the lowest at the 36th week of pregnancy. Women in surgical menopause reported higher pain intensity as well as more difficulties with chewing and eating hard and soft food compared to the other subjects. Depressive symptoms and somatization were lowest among the women with advanced pregnancy and the highest among menopausal women. Conclusion: TMD-related chronic pain grade, masticatory dysfunction, and depressive symptoms and somatization are the highest when the estrogen level is the lowest. Keywords: chronic pain, estrogen, menstrual status, surgical menopause, temporomandibular disorders