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Simple Summary: Background: It is challenging to differentiate between enchondromas and atypical cartilaginous tumors (ACTs)/chondrosarcomas. Methods: To evaluate the diagnostic usefulness of radiological findings for differentiation between enchondromas and chondrosarcomas, correlations between various radiological findings and final diagnoses were investigated. Based on the correlations, a scoring system combining these findings was developed. Results: In a cohort of 81 patients, periosteal reaction on X-ray, endosteal scalloping and cortical defect on CT, extraskeletal mass, multilobular lesion, abnormal signal in adjacent tissue on MRI, and increased uptake in bone scan and thallium scan was significantly correlated with final diagnoses. Based on the correlations, a radiological scoring system combining radiological findings was developed. In another cohort of 17 patients, the sensitivity, specificity, and accuracy of the radiological score rates for differentiation between enchondromas and chondrosarcomas were 88%, 89%, and 88%, respectively. Conclusion: Comprehensive assessment combining radiological findings is recommended to differentiate between enchondromas and ACTs/chondrosarcomas. Background: It is challenging to differentiate between enchondromas and atypical cartilaginous tumors (ACTs)/chondrosarcomas. In this study, correlations between radiological findings and final diagnosis were investigated in patients with central cartilaginous tumors. Methods: To evaluate the diagnostic usefulness of radiological findings, correlations between various radiological findings and final diagnoses were investigated in a cohort of 81 patients. Furthermore, a new radiological scoring system was developed by combining radiological findings. Results: Periosteal reaction on X-ray (p = 0.025), endosteal scalloping (p = 0.010) and cortical defect (p = 0.002) on CT, extraskeletal mass (p < 0.001), multilobular lesion (p < 0.001), abnormal signal in adjacent tissue (p = 0.004) on MRI, and increased uptake in bone scan (p = 0.002) and thallium scan (p = 0.027) was significantly correlated with final diagnoses. Based on the correlations between each radiological finding and postoperative histological diagnosis, a radiological scoring system combining these findings was developed. In another cohort of 17 patients, the sensitivity, specificity, and accuracy of the radiological score rates for differentiation between enchondromas and ACTs/chondrosarcomas were 88%, 89%, and 88%, respectively (p = 0.003). Conclusion: Radiological assessment with combined radiological findings is recommended to differentiate between enchondromas and ACT/chondrosarcomas. [ABSTRACT FROM AUTHOR]