A clinical and epidemiological investigation was performed on 62 adolescents, 21 males and 41 females, with recurring headaches, in order to analyze the connections between the cephalalgia and the signs and symptoms of mandibular dysfunction. The anamnestic and objective data were reviewed with the aid of the Helkimo indices and compared to data on a control group of comparable age who were not headache sufferers. The most statistically significant signs encountered (p < 0.001) were: pain on palpation of masticatory muscles (61%), altered (43%) or reduced (27%) mandibular movement, preauricular tenderness (19%); the high incidence of parafunctions indicated the behavioral substrate. This pilot study reveals a link between the two pathologies and the need for early diagnosis, preventive identification of the subjects at risk and interdisciplinary cooperation.