Trigeminal trophic syndrome (TTS) is an uncommon condition characterised by anaesthesia, paraesthesias and ala nasi ulceration, following peripheral or central damage to the trigeminal nerve. Only about 100 cases have been described in the literature to date. We report a 74-year-old woman who presented with a right cheek ulcer accompanied by pruritus and paraesthesia for three months. An old right cerebellar infarct was demonstrated on magnetic resonance imaging of the brain. Vertebrobasilar insufficiency leading to the cerebellar infarct is likely to have predisposed her to developing TTS. An underlying infectious, malignant and vasculitic cause for the ulcer was excluded by a skin biopsy. An increased awareness of the predisposing factors and clinical presentations of this important disfiguring condition is necessary to ensure prompt diagnosis and treatment.