Although uncommon in many pathology practices, cartilage-forming tumors represent some of the most frequent primary bone tumors. Diagnosis can be challenging given their variable histologic spectrum and the presence of overlapping morphologic, immunohistochemical, and genetic features between benign and malignant entities, particularly low-grade malignancies. Correlation with clinical findings and radiographic features is crucial for achieving an accurate diagnosis and appropriate clinical management, ranging from observation to excision. Tumors can be characterized broadly by their location in relation to the bone (surface or intramedullary). In specific instances, ancillary testing may help.