Simultaneous pneumoperitoneum and pneumomediastinum is a rare clinical occurrence. It has been reported in the literature as a complication of various medical and dental procedures. To our knowledge, we present the first case of a non-iatrogenic and traumatic simultaneous pneumoperitoneum and pneumomediastinum in a previously independent 91-year-old man who presented to hospital with back and chest wall pain following mechanical fall from standing. A new radiological diagnosis of diverticular disease with possible perforation was made following admission. Despite appropriate management and supportive measures, the patient died 12 days after admission from a kidney injury.