Enchondroma and chondrosarcoma are two of the most commonly encountered primary bone lesions in the typical radiology practice. The purpose of this article is to review the clinical, radiological, and pathological features that distinguish conventional chondrosarcoma from enchondroma. Chondrosarcoma is almost always associated with pain and tends to present in the axial skeleton of middle aged adults. Enchondroma tends to present in young adults in the appendicular skeleton, particularly the hands, and is often an incidental finding. Although both lesions have characteristic radiographic appearances, difficulty separating these two entities most often occurs when a lesion is seen in the long tubular bones. The judicious use of computed tomography, magnetic resonance imaging, and nuclear medicine in conjunction with appropriate clinical data allows the radiologist to establish the correct diagnosis of benign or malignant medullary chondroid lesion in the majority of cases.