The greater wings of the sphenoid bone (GWS) comprise the components of the sphenoid bone that make up most of the posterior orbital wall and form the anterior and medial parts of the floor of the middle cranial fossa. Many important skull base foramina, which transmit vital neurovascular structures, are present in these paired wings on either side of the central body of the sphenoid bone. A wide variety of diseases can affect the GWS, ranging from benign osseus lesions to malignant primary and secondary bone abnormalities. The complex three-dimensional curved (winged) shape of the GWS and the wide array of pathologic entities that affect this bone can make it challenging for the radiologist to report the imaging findings accurately, especially in relation to the important skull base foramina. The authors describe a systematic approach to understanding the three-dimensional anatomy of the GWS and review important diseases, with the aid of imaging examples. Useful imaging "pearls" that can help in making specific diagnoses are provided throughout the article. ©RSNA, 2022.