Acute cerebral stroke is a leading cause of disability and death, which could be reduced with a prompt diagnosis during patient transportation to the hospital. A portable retina imaging system could enable this by measuring vascular information and blood perfusion in the retina and, due to the homology between retinal and cerebral vessels, infer if a cerebral stroke is underway. However, the feasibility of this strategy, the imaging features, and retina imaging modalities to do this are not clear. In this work, we show initial evidence of the feasibility of this approach by training machine learning models using feature engineering and self-supervised learning retina features extracted from OCT-A and fundus images to classify controls and acute stroke patients. Models based on macular microvasculature density features achieved an area under the receiver operating characteristic curve (AUC) of 0.87–0.88. Self-supervised deep learning models were able to generate features resulting in AUCs ranging from 0.66 to 0.81. While further work is needed for the final proof for a diagnostic system, these results indicate that microvasculature density features from OCT-A images have the potential to be used to diagnose acute cerebral stroke from the retina.