OBJECTIVE. The purpose of this study was to determine whether the imaging features of periosteal chondroid tumors correlate with histopathology. MATERIALS AND METHODS. Twenty-two patients (nine women and 13 men; mean age, 33 years) with pathologically proven periosteal chondroid lesions were retrospectively reviewed. The imaging modalities included conventional radiography (n = 17), CT (n = 10), and MR imaging (n = 14). The images were reviewed by two osteoradiologists, with agreement by consensus. Evaluation criteria included lesion location, mineralization, and size; periosteal reaction; and cortical response. Intramedullary extension, adjacent intramedullary edema, soft-tissue edema, and intrinsic characteristics were also evaluated on MR imaging. After the evaluation, a radiologic diagnosis of chondroma or chondrosarcoma was obtained. An experienced osteopathologist who was unaware of the patient's medical history and radiologic findings reviewed all histopathology. Agreement between the radiologic and the histopathologic diagnosis was tested using the kappa analysis. Imaging features were correlated with the pathologic findings, and a statistical analysis was performed. RESULTS. Using strict pathologic criteria, we diagnosed 11 chondromas and 11 chondrosarcomas (nine, grade I; two, grade II). Moderate agreement was reached between the radiologic and the pathologic diagnosis (κ = 0.55). The size of periosteal chondrosarcomas (range, 3-14 cm; median, 4 cm) was considerably larger than the size of the chondromas (range, 1-6.5 cm; median, 2.5 cm: p < 0.05). Other imaging features did not significantly correlate with benign versus malignant disease at pathology (all p > 0.05). CONCLUSION. A variable overlap existed in the imaging appearances of benign and malignant periosteal chondroid lesions, with size being the most reliable indicator in distinguishing the two lesions. This and the fact that histologic differentiation of the entities can be difficult, suggests that surgical wide excision may be the most appropriate procedure in treating patients with lesions greater then 3 cm.