The purpose of this article was to review the anatomy of the cavernous sinus (CS), illustrate numerous lesions that can affect the CS, and emphasize the imaging characteristics for each lesion to further refine the differential diagnoses. The CS, notwithstanding its small size, contains a complicated and crucial network that consists of the carotid artery, the venous plexus, and cranial nerves. The wide-ranging types of pathologies that can involve the CS can be roughly classified as tumoral, congenital, infectious/inflammatory/granulomatous, and vascular. Conditions that affect the CS usually lead to symptoms that are similar to each other; thus, for diagnosis, imaging procedures are required. Radiological evaluations are also required to detect pre- and postoperative CS invasion. Magnetic resonance imaging, which can be supplemented with thin-section contrast-enhanced sequences, is the preferred imaging technique for evaluating the CS. For correct diagnosis of CS lesions and accurate evaluations of CS invasions, it is essential to carefully analyze the anatomical structures within the CS and to acquire precise knowledge about the imaging features of CS lesions, which may frequently overlap.