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Pathologic uterine rings, also called Bandl’s ring, are historically associated with obstructed labor and good neonatal outcomes.Two cases are presented involving a pathologic uterine ring identified at cesarean delivery, which led to fetal cranial trauma. At delivery, pathologic uterine rings were found to encompass the heads of both fetuses, with gross features of traumatic head deformity. Radiologic studies demonstrated intracranial hemorrhage predating delivery. Both infants developed cerebral palsy, which was initially attributed to hypoxic-ischemic encephalopathy from delivery despite normal umbilical arterial pH. Further investigation linked the intracranial bleeding to compressive trauma from the uterine rings.Although rare, pathologic uterine rings may cause traumatic cranial deformity and subsequent cerebral palsy.