Headache can be caused by a multitude of factors, but experienced physicians accustomed to treating patients with headache are adept at making an accurate diagnosis. Occasionally, however, a patient has an unusual presentation of headache or facial pain. In these cases, it can be difficult to classify the etiology of the headache despite the performance of a thorough physical examination and the acquisition of appropriate diagnostic tests. Awareness of some of the otolaryngologic diseases that can manifest as facial pain or headache may help the physician better diagnose and treat this complex problem.