Introduction. Spontaneous intramural oesophageal haematoma is a rare condition that usually occurs secondary to an acute or chronic coagulation disorder. The presenting complaint is often with retrosternal chest pain and most patients are initially investigated to exclude more common causes in the differential diagnosis, such as acute coronary syndromes. Severe life-threatening bleeding or perforation seldom, if ever, arises. Case Presentation. We present a case of spontaneous oesophageal haematoma which appears to have developed gradually in a 69-year-old female with uncontrolled hypertension and antiplatelet medication use. The diagnosis was made on computed tomography imaging and was further evaluated with upper gastrointestinal endoscopy. Management was conservative and a follow-up endoscopy two weeks later showed almost complete resolution of the lesion. Discussion. Spontaneous oesophageal haematomas are very rare and usually result in the separation of the mucosal layer from the underlying muscle, presenting with chest pain, haematemesis, and dysphagia. Usually the diagnosis is one of exclusion, based on computed tomography imaging and endoscopy. Conservative management is almost always successful.