Spontaneous retropharyngeal haematoma and dissecting intramural haematoma of the oesophagus are two distinct, but rare, phenomena. We describe the first case of complete tracheo-oesophageal obstruction due to spontaneous retropharyngeal haematoma presenting with chest pain and dysphagia. Rapid imaging allowed life-saving transfer to the regional specialist centre, with immediate surgical intervention. The importance, aetiology and clinical features of both diagnoses are discussed.