Aims and Objectives:Temporomandibular joint disorder (TMD) is an umbrella term for a number of conditions in the area of the joint, temple, and masticatory system. Many of those with TMD also suffer from headaches and anxiety. The aims and objectives of this study were to determine if there exists an association between the Diagnostic Criteria of TMD (DC/TMD) symptom questionnaire and report of headaches as well as stress.Materials and Methods:A cross-sectional study was implemented via the use of the DC/TMD symptom questionnaire and the perceived stress scale (PSS). This was distributed conveniently among dental students in a multi-dental school setting in Riyadh, Saudi Arabia, and was completed by 152 dental students. Odds ratios, Chi-square, and their corresponding 95% confidence intervals are reported. Statistical significance was set at P ≤ 0.05.Results:Those who ticked yes for pain on the TMD pain screener for pain with chewing hard or tough food, pain on mouth opening and lateral excursion, and pain with jaw habits as parafunction were at an odds risk from twice to thrice as likely to experience headaches. Similarly, those with poor coping skills on the PSS were more likely to have headaches (P = 0.002). Likewise, positive answers on the screener and symptom questionnaire were relevant with higher stress scores on the PSS.Conclusion:This study clarifies and reiterates the intertwined power of both stress and headaches; the former being a role player in TMD progression and the latter its product. TMD is unfortunately on the rise; it should not be brushed off as a nuisance. A multidisciplinary approach in diagnosis and treatment of both TMD and headaches by a team of orofacial pain specialist, neurologist, psychiatrist and/or psychologist, and physical therapists to untangle the deceiving presentation of both conditions would not only provide a more favorable prognosis but also improve cost and time expenditures.