Carotid hypersensitivity syndrome (CHS) is characterized by recurrent syncope in response to carotid sinus receptor stimulation. It is common in older adult males. Due to recurrent syncope and falls, these patients often present with acute-on-chronic subdural hematoma (SDH). Diagnosing CHS is often challenging, especially in patients with SDH who present with signs of elevated intracranial pressure. Proceeding to anesthetize the patient without evaluating the cause of syncope can lead to perioperative morbidity and mortality. Here, we report the perioperative management of an elderly gentleman who presented with recurrent syncope and falls leading to bilateral SDH and was systematically evaluated and diagnosed with CHS based on the head-up tilt test and carotid sinus massage. He underwent temporary cardiac pacemaker insertion followed by evacuation of bilateral SDH under monitored anesthesia care and a scalp block. Later, he underwent permanent cardiac pacemaker insertion for CHS. Coordinated multidisciplinary care facilitated faster recovery without morbidity.