Case reports in the literature discuss various headache disorders that present as pain in the face. The current understanding of neuroanatomy and headache mechanisms suggests that headache pain originates within intracranial structures and is then referred to the face, jaws, and teeth. This case series describes four patients, one each with migraine headache, cluster headache, paroxysmal hemicrania, and hemicrania continua, all of which who presented to dentists with the chief complaint of tooth pain. This is the first report of hemicrania continua presenting as tooth pain. It is important that dentists be cognizant of headache disorders so that they may be able to identify headache pains masquerading as toothache.