This chapter, written for undergraduate medical students and post-graduate doctors in training, presents information on how to manage facial pain — a case which they are likely to encounter in the future in a general practice setting. It presents the case of a 55-year-old woman, married with three grown children, who has been experiencing pain in the left side of her face for some months. It is not constant, but can last for an hour or two when it comes; it is severe, throbbing and stabbing in character; and seems to arise in the cheek, radiating down to the side of her jaw and neck. The chapter provides details of the patients' medical history and the key findings of clinical examination, together with initial investigation results data for evaluation, and helps them develop their skills of clinical reasoning. Key questions then prompt the student to evaluate the patient, and reach a decision regarding their condition and the possible treatment plan.