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Introduction: The incidence of stroke is higher in patients with malignancy, especially within a few months of diagnosis and in more aggressive cancers. This phenomenon may be explained by an inherent hypercoagulable state, tumor embolism, vessel infiltration, or as a side effect from cancer treatment. Notably, stroke in cancer patients is associated with poor functional outcomes and reduced survival. Currently, however, there are no clear guidelines for antithrombotic management for prevention of recurrent strokes in these patients. Methods: We conducted a single-center retrospective chart review from 2013-2019. All adult patients with an ischemic stroke occurring with active malignancy and who then received either a direct oral anticoagulant (DOAC) or low molecular weight heparin (LMWH) were included. Patients with hemorrhagic stroke, an intracranial malignancy, or who were immediately admitted to hospice were excluded. Results: A total of 55 patients were included with a mean age of 71.8 years (range 28-96), 60% females, 87.3% first-time strokes, and 54.9% with metastatic disease. After stroke, 25 patients received a DOAC and 30 received LMWH for anticoagulation with a mean follow-up of 403 days. Between these two groups, most presentation and treatment characteristics were similar except for baseline hypertension, hyperlipidemia, additional initiation of an antiplatelet, and follow-up time. There was no difference in either stroke recurrence (DOAC vs LMWH: OR 2.61 [0.51-13.45], p=0.252) or time to recurrent stroke (DOAC vs LMWH: HR 1.68, p=0.446), but both analyses required adjustment for additional initiation of an antiplatelet—which was significantly protective regardless of anticoagulation choice (p=0.021* and p=0.017*, respectively). There was a trend towards improved survival if placed on a DOAC (HR 0.27, p=0.051), even after adjusting for metastatic disease. Conclusions: In this initial study of cancer patients with ischemic stroke, anticoagulation choice made no difference on stroke recurrence; however, addition of an antiplatelet agent was significantly protective. There was also a trend towards improved survival on a DOAC. Additional prospective data incorporating a larger sample size could further validate these findings.