Intramural hematoma is commonly known as a hematoma that occurs in the wall of a structure, such as the bowel or bladder, usually resulting from trauma or, in rare situations, excessive anticoagulation. In particular, intramural gastrointestinal hematoma is part of a spectrum of gastrointestinal injuries. Vomiting and straining, endoscopic procedures, and bleeding disorders are essentially among the most common predisposing factors. However, it can also be an unusual complication of anticoagulation and/or thrombolysis therapy. The most common symptoms are retrosternal chest pain, dysphagia, and hematemesis. Intramural bowel wall hematoma is an often forgotten, rare clinical entity that may pose considerable diagnostic dilemma. Therefore, it is conspicuously imperative to diagnose this condition promptly and correctly in order to avoid unnecessary surgical intervention. In this rare presented case report, a 51-year-old woman having mitral valve prothesis and mild heart failure under warfarin wasadmitted to the renowned Sahel General Hospital in Beirut in November of 2006 with massive upper gastrointestinal bleeding that was subsequently controlled by endoscopic sclerotherapy and medical management. About 12 h later, the aforementioned patientsuffered a severe abdominal pain accompanied by a steep dropping in the hematocrit level. Moreover, an abdominal computed tomography scan showed thick jejunal hematoma of approximately 70 cm in length that was handled surgically. The patient had been incessantly observed for about 7 days,andsubsequently discharged with therapeutic international normalized ratio(INR).