<p>Histological examination of central cartilage tumors (enchondromas, atypical cartilage tumors or ACTs, or grade I, II and III chondrosarcomas or CSs and dedifferentiated CS) is often inadequate, both because the biopsy sample may not be representative of the entire tumor and due to the intrinsic limitations of the method itself, which frequently underestimates the grade of CS or even misclassifies it as benign. In the diagnosis of cartilaginous tumors, radiological assessment is generally considered superior to histology. Radiological investigations allow for the identification of the cartilaginous origin of a central bone lesion through the detection of cartilaginous matrix and other signs such as globular calcifications, endosteal scalloping and fat entrapment, more frequent in enchondroma and ACT. Radiological features of aggressiveness—such as cortical disruption with soft tissue invasion, perilesional edema, periosteal reaction, enlargement of the skeletal segment, absence of matrix calcifications, and lack of fat entrapment—are indicative of high-grade CS (II and III grade CS, dedifferentiated CS). However, due to the overlap in radiological appearances between enchondromas/ACTs and low-grade/high-grade CSs, it is essential to correlate imaging findings with clinical and pathological data in order to accurately classify the lesion and define an appropriate diagnostic and therapeutic strategy.</p>