Osteoid osteoma (OO) is a common benign bone tumour, usually affecting young people. Typically, it is localised to the diaphyses or metaphyses of long bones. The classical manifestation includes distinctive night pain, almost always present, responding well to non-steroidal anti-inflammatory drugs, sometimes accompanied by complaints due to physical activity, and a typical picture on additional tests. A characteristic of osteoid osteoma is the presence of a nidus, usually visible on imaging tests. The nidus generally presents as a single, round lytic lesion up to 1 cm in diameter, surrounded by an area of reactive ossification. However, OO is a multifaceted neoplasm, and its diagnosis can cause numerous difficulties. OO can mimic multiple diseases and vice versa, which often leads to a prolonged diagnostic and therapeutic path and associated complications. There are few literature reviews about the differentiation and diagnostic difficulties of osteoid osteoma. Very effective therapies for this tumour are known, such as ablation and resection. Enhanced detection of osteoid osteoma could result in faster diagnosis and less suffering for the patient, avoidance of complications, and reduced costs of incorrect and prolonged treatment.