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There is growing evidence in support of ischemic stroke as a manifestation of COVID-19 infection. However, hemorrhagic transformation of ischemic stroke is rare. We present two cases of hemorrhagic infarction as presenting features in COVID-19 patients who did not have traditional cardiovascular risk factors for ischemic or hemorrhagic stroke. While the hemorrhagic infarct was from a large artery in one of the patients, the other patient had a small artery related hemorrhagic infarct. We highlighted the possible underlining mechanisms from the literature and the implication of hemorrhagic infarct for routine anticoagulant therapy in patients with COVID −19 related ischemic stroke.