Ossifying fibromas (OFs) are benign, well-demarcated lesions in the craniofacial region, particularly in the jaws, with clinical, radiographic, and histopathological similarities to other lesions, which make their diagnosis challenging. Herein, we report a case of a fibro-osseous lesion in the anterior maxilla of a 13-year-old boy, consisting of an intraosseous and an extra-osseous part, which created a diagnostic dilemma.