Persistent left superior vena cava (PLSVC) can lead to thromboembolic phenomena including transient ischaemic attacks and stroke. This case report signifies the importance of its identification through simple investigations like echocardiography. The management of this condition described in literature is predominantly surgical. Treatment of this condition with anticoagulation, as described in our paper is a novel approach in managing this condition. A 64-year-old man with a background of dyslipidemia and hypertension presented with symptoms of aphasia and confusion. He was diagnosed with a bi-hemispheric stroke on MRI brain. A transoesophageal echocardiogram was performed as a part of the stroke work up. A bolus of agitated gelofusine administered via a left-sided cannula showed immediate contrast opacification of the left atrium before the right atrium, indicative of a venous to systemic shunt. When agitated gelofusine was injected via the right arm, normal contrast filling was demonstrated in the right atrium first. A cardiac CT confirmed the presence of a PLSVC draining into the left side of the heart. He was commenced on apixaban as secondary prevention for recurrent paradoxical embolisation and remains symptom free one year after initial presentation. In a setting of cryptogenic stroke, a venous-to-arterial shunt caused by a PLSVC should be considered as a potential source of embolus. Echocardiography with contrast injections from both arms should be carried out to assess possible anomalous thoracic venous drainage. Making the diagnosis of venous-to-systemic shunt would help formulate appropriate management to prevent recurrence of embolic phenomena.