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Osteoid osteomas are common, benign osteoblastic tumors that can occur in any bone in the body. They are almost always solitary, with only rare reports of multiple tumors in the same patient. When multiple, they typically are found within the same bone. We present a unique case of a young female athlete who presented initially at 16 years old with a right tibial osteoid osteoma and later at 18 years old with a right acetabular osteoid osteoma. Our case demonstrates the rare entity of polyostotic osteoid osteoma, the potential limitations of MRI in the diagnosis of osteoid osteoma, and the utility of radiofrequency ablation in the treatment of osteoid osteoma. Keywords: Benign bone tumor, Osteoid osteoma, Multifocal, Multicentric, Metachronous, Radiofrequency ablation