Objective This article describes an atypical herpes zoster (HZ) infection heralded by prodromic dental pain. Background Trigeminal HZ is associated with any of the three divisions of the trigeminal nerve, and Ramsay Hunt syndrome is a rare variant of HZ infection of the ear, often accompanied with unilateral facial nerve palsy. Materials and methods An 87‐year‐old man sought remedy for tooth‐like pain. Within a week, he developed cutaneous, intraoral and otic eruptions, hearing loss, and mild facial palsy. Results After ruling out odontogenic pain, he was diagnosed with trigeminal HZ and Ramsay Hunt syndrome. Conclusion Herpes zoster infection should be included as a possible aetiologic factor with atypical presentations of odontogenic pain. Diagnosis of trigeminal HZ infection and the Ramsay Hunt syndrome may lead to timely intervention with antivirals and improved patient outcomes.