Symptomatic intratumoral hemorrhage (ITH) in vestibular schwannoma (VS) is rare. A repeated hemorrhage is, therefore, even more exceptional. Repeated ITH has been reported in four cases thus far in English literature. Here, we describe a patient with a Koos grade D VS who presented to our Skull Base team with repeated ITH and an unexpected disease course.A 76-year-old woman presented with hearing loss due to polycystic VS on the left side. Five years later, the patient was presented with facial palsy caused by hemorrhage in the VS. The patient had an eventful medical history that necessitated the use of anti-coagulants. The patient suffered from three subsequent hemorrhages preoperatively and one hemorrhage 36 h postoperatively.We have experienced multiple repeated hemorrhages in a patient with a polycystic VS, and despite surgical intervention, the outcome was unfavorable.