Abstract : Introduction Long-term anticoagulation is associated with hemorrhage at various sites. Gastrointestinal intramural bleeds and hematomas (IMH) often mimic mesenteric ischemia (MI) due to similar clinical settings and imaging features, making early differentiation difficult. Aim To compare the demography, clinical features and imaging characteristics of patients presenting with IMH with those of MI, so as to help in evolving clinical and imaging guidelines to differentiate both early in the course of the disease. Methods All radiologically (contrast-enhanced computed tomogram [CT]) diagnosed cases of gastrointestinal IMH from the hospital database during the period between 2006 and 2012 were retrospectively analyzed. This data was compared with the clinical and imaging features of a group of surgically confirmed MI during the same period. Patients not on anticoagulation therapy at the time of presentation and those with incomplete clinical or radiological data were excluded from the study. Results There were 16 patients in IMH group and 54 patients in MI group. Clinical features like overt rectal bleeding or melena, and prolonged prothrombin time-international normalized ratio (PT-INR) more than three, and CT features like proximal location in the bowel, increased bowel wall thickness, hyperdensity on plain scan (40 Hounsfield units (HU)), and short segment bowel involvement were significantly associated with IMH. Visualization of embolus and absent mesenteric vasculature to a segment of intestine in CT was significantly associated with MI. Conclusion Attention to clinical features and early CT scan can aid in early differentiation of IMH from MI, facilitating appropriate intervention early in the course of disease. © 2014 Indian Society of Gastroenterology.