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Anastomosing hemangioma is a benign vascular neoplasm originally described in the genitourinary tract, but subsequently reported in a variety of anatomic sites. Although ovarian involvement has been documented, bilateral localization has not yet been reported in the English literature. Here, we describe the case of a 67-year-old woman with a strong clinical suspicion of advanced ovarian carcinoma, in whom histologic examination revealed bilateral ovarian anastomosing hemangioma. Frozen section evaluation did not allow a definitive diagnosis; however, on permanent sections, characteristic diagnostic features-such as foci of extramedullary hematopoiesis and scattered fibrin thrombi-became evident, enabling the correct classification. This report highlights the peculiar presentation of bilateral ovarian anastomosing hemangioma, aiming to increase awareness of this rare entity and to emphasize the diagnostic challenges it may pose, particularly during intraoperative consultation.