Background: Ischemic stroke secondary to NBTE is a rare complication of systemic malignancies. Although previously reported in gynecological cancers, this occurrence is infrequent. Furthermore, stroke pre-dating the gynecological malignancy diagnosis has rarely been reported. Methods: Case presentations and literature review. Results: Case1: A 48-year-old woman presented with acute dysarthria and left facial weakness caused by a right middle cerebral artery (MCA) infarct. Mitral valve vegetations were found on a transthoracic echocardiogram (TTE). A malignancy screen uncovered a pelvic endometrial adenocarcinoma. Case 2: A 49-year-old woman developed acute right hand weakness. A CT head scan showed a left pre-central gyrus infarct. Her TEE revealed aortic valve vegetations. An ovarian neoplasm was then discovered. Case 3: A 36-year-old woman with a known diagnosis of cervical squamous cell carcinoma developed acute left-sided weakness secondary to a right MCA stroke. Aortic valve vegetations were seen on TTE. Conclusions: We have reported three cases of NBTE where the underlying malignancy was gynecological. In the first two cases, the malignancy was discovered while investigating for the stroke mechanism, while the third had a known underlying malignancy. This series highlights the need to consider gynecological malignancies as an underlying cause of stroke in young women; and that the ischemic event can occur prior to the malignancy diagnosis.