A variation in the usual course of great vessels during neck dissection can predispose them to inadvertent iatrogenic injury, which can lead to massive bleeding. We present a case of a male patient with oral squamous cell carcinoma who underwent inferior maxillectomy and supra-omohyoid neck dissection. Lateral coiling of the extracranial internal carotid artery was seen through fenestration of the internal jugular vein. Anomalies of great vessels in the neck are rare. Variation in the course of any of these vessels can prove to be catastrophic if control is not achieved. Careful study of radiographic imaging with special consideration given to the course of great vessels in the neck should be undertaken prior to neck surgeries.