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Clear cell chondrosarcoma (CCCS) is a rare variant of conventional chondrosarcoma with low-grade malignant features that may be confused radiographically and histologically with chondroblastoma. We report a case of a 50-year-old female who presented with 6 months of left hip pain. Initial radiographs demonstrated an osteolytic lesion with adjacent area of sclerosis in the proximal left femur. Magnetic resonance imaging demonstrated a marrow-infiltrative lesion with periosteal reaction and thickened enhancing periosteum. Biopsy of the sclerotic area demonstrated chondroblastoma-like findings, whereas biopsy of the lytic area showed features suggestive of CCCS. The patient eventually underwent en bloc resection and reconstruction with a proximal femoral megaprosthesis. The final diagnosis was CCCS. We present this unusual case with review of the radiographic and histologic features of CCCS with attention to its ability to mimic chondroblastomas. This case highlights the importance of sampling radiographically heterogeneous areas within a bone lesion to facilitate accurate diagnosis and appropriate management.