Spontaneous iliac vein rupture (SIVR) is a rare entity, which usually occurs without a precipitating factor, but can be a life-threatening emergency often requiring an emergency operation. This is a case report of SIVR in a 62-year-old female who presented to the emergency room with left leg swelling. Workup with contrast-enhanced computed tomography revealed a left leg deep vein thrombosis with May-Thurner syndrome and a hematoma in the pelvic cavity without definite evidence of arterial bleeding. She was managed conservatively without surgical intervention, and also underwent inferior vena cava filter insertion and subsequent anticoagulation therapy for pulmonary thromboembolism. This case shows that SIVR can be successfully managed with close monitoring and conservative management, and anticoagulation may be safely applied despite the patient presenting with venous bleeding.