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Osteoid osteoma is a primary benign bone tumor that consists of a central area (nidus), surrounded by sclerotic bone. The most relevant symptom is pain that increases during the night and improves after salicylates or nonsteroidal anti-inflammatory drug administration. Osteoid osteoma is frequently misdiagnosed because it mimics juvenile idiopathic arthritis, bone infection, or malignancy. A 14-year-old girl presented to our department with a history of chronic pain in her left ankle. Juvenile idiopathic arthritis was diagnosed and anti-inflammatory treatment was prescribed. Because of persistence of ankle pain, the patient underwent further examinations, in particular, bone scintigraphy and computed tomography. As a result, osteoid osteoma of the talar neck was diagnosed. The patient underwent surgical treatment and her condition improved. Osteoid osteoma should also be considered in patients with chronic ankle pain to avoid misdiagnosis and start adequate treatment. This condition should be suspected in a patient with chronic bone pain and normal complete blood count and inflammatory parameters.