A 78 year old gentleman on anti-platelet (Clopidogrel) therapy presented with uni-ocular visual impairment and ipsilateral non-pulsatile progressive proptosis. MRI (magnetic resonance imaging) brain showed an intra-Diploic expansile lytic lesion which had homogenous hyper intensity on T1 weighted images and heterogeneous intensity on T2 weighted images. Histopathology was suggestive of an organizing hematoma. Intra-Diploic hematoma, though mimicking Aneurysmal bone cyst is a different clinico-pathological entity. The etiology and pathogenesis of this rare clinical entity is discussed.