Aim. Headache is one of the most common diseases associated with Temporomandibular Disorders (TMDs). The aim of this study was to evaluate, retrospectively, if headache influences TMD's symptoms. Material and Methods. A total sample of 1198 consecutive TMD patients was selected. After a neurological examination, a diagnosis of headache, according to the latest edition of the International Classification of Headache Disorders, was performed in 625 subjects. Patients were divided into two groups based on presence/absence of headache: Group with Headache (GwH) and Group without Headache (GwoH). Descriptive statistics and Chi-square index were performed. Results. Sociodemographic (gender, marital status, and occupation) and functional factors, occlusion (occlusal and skeletal classes, dental formula, and occlusal abnormalities), and familiar pain did not show a statistically significant correlation in either group. Intensity and frequency of neck pain, arthralgia of TMJ, and myalgia showed higher correlation values in GwH. Conclusion. This study is consistent with previous literature in showing a close relationship between headache and TMD. All data underlines that headache makes pain parameters more intense and frequent. Therefore, an early and multidisciplinary treatment of TMDs should be performed in order to avoid the overlay of painful events that could result in pain chronicity.