We present an uncommon case of a patient presenting at the emergency department for severe vomiting, persisting for at least 12 hours, without nausea or abdominal pain. She initially referred vomiting food eaten several hours earlier and eventually a single episode of haematemesis with emission of a small amount of red blood and clots. She also reported the occurrence of acute dysphagia for solid food. The patient underwent oesophagogastroduodenoscopy (OGD), which showed that the lumen was almost completely narrowed by a submucosal bluish bulging from midoesophagus (19 cm from the incisors) to the cardia (located at 35 cm from the incisors). She therefore underwent chest CT showing a 15 cm long intramural oesophageal haematoma. Although the combination of vomiting and haematemesis is usually associated with Mallory-Weiss syndrome, in which a prompt OGD has a key role in the patient management, when these symptoms are associated with acute dysphagia, a possible intramural haematoma might be suspected. In this case, chest CT should take precedence, because it allows a quick and complete diagnostic appraisal. However, in this setting, although OGD can directly show typical findings (bluish swelling mucosa with or without a superficial tears), it might increase the risk of oesophageal haematoma rupture and intraluminal bleeding.