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Iliac vein rupture is a rare cause of retroperitoneal hemorrhage. It is occasionally lethal, with no clear precipitating factors. We report a case of spontaneous left common iliac vein rupture in a 56-year-old man with a history of deep vein thrombophlebitis (DVT). To date, 32 cases have been reported in the literature. The 32 existing cases and the case presented here were analyzed. A comparative review was performed for chief complaints, basic demographics, potential predisposing factors, treatment modalities, and outcomes. Possible etiological factors to explain this phenomenon were formulated. The patient presented with abdominal pain of 4 hr duration and a near-syncope episode. In the emergency room, he was found to be in hypovolemic shock that was responsive to crystalloids. An urgent exploratory laparotomy was performed for a suspected iliac artery rupture. An uncontrollable hemorrhage from a spontaneous posteromedial tear of the left common iliac vein resulted in intraoperative death. Interestingly, 85% of reported cases occurred in women with an overall average age of 60.6 +/- 13.4 years; 94% of cases were left-sided; 79% reported clinical or histological evidence of DVT or thrombophlebitis; 94% were treated operatively, with a survival rate of 71%. Only one reported case was treated conservatively, with success, and one reported case of endovascular repair resulted in significant morbidity. Iliac vein rupture is an uncommon diagnosis associated with trauma and even rarer when it is spontaneous. We report the thirty-third documented case in the literature since 1961. There is a clear predominance in females and on the left side and a probable association with thrombophlebitis. Our calculated operative success may be overestimated due to a biased literature reporting of favorable outcomes.