Aims: To investigate the prevalence and overlaps of headaches and pain-related temporomandibular disorders (TMD) among the Polish urban population. Methods: The study was conducted in four Polish cities (Wroclaw, Lublin, Katowice, and Lodz) between February and November 2017. Participation in the study was voluntary. The examination consisted of two parts: a clinical examination of TMD using the Diagnostic Criteria for TMD Examination Form and the Head-HUNT Study questionnaire filled in by the participants to determine the occurrence and type of headaches. An experienced and qualified clinician trained all the examiners in the clinical examination protocol. Statistical analyses were based on descriptive and nonparametric statistics. In addition, univariate logistic regression was used. The significance level was set at α = .05. Results: Overall, 213 individuals were examined (149 women and 64 men). The mean age of the participants was 37 ± 15.82 years. The diagnosis for 55.9% of the participants was pain-related TMD, including myalgia (47.4%), myofascial pain (14.1%), arthralgia (21.1%), or headache attributed to TMD (10.3%). In the study population, 48.8% were diagnosed with temporomandibular joint disorders, most frequently disc displacement with reduction (47.9%). A total of 73% of the individuals had experienced headaches in the previous 12 months. The majority of the participants described the headache episodes as occurring less than 7 days/month and lasting less than 4 hours. Among people with painful TMD, the frequency of headaches was almost twice as high as that in nondisordered individuals (48.35% and 25.35%, respectively; P < .0001). The logistic regression model confirmed a significant overlap between headache and painful TMD (OR = 4.77, 95% CI 2.44–9.32, P = .0000). For the entire studied population, no statistically significant connections were established between the occurrence of identified TMJ disorders and headache reports or diagnoses (P > .05). Conclusion: Headaches and pain-related TMD are major problems among the Polish urban population. Headache was a much more frequent problem for participants with painful TMD. This issue requires further research and identification of cause-and-effect relationships. Considering the entire studied population, the relationship between identified TMJ disorders and headache is negligible.