Juvenile psammomatoid ossifying fibroma (JPOF) is a rare, benign yet locally aggressive fibro-osseous tumor that can affect the craniofacial skeleton in young patients. Its presentation can be atypical, often complicating diagnosis and management. Case Presentation: A 14-year-old presented with a history of right ear trauma sustained during rugby, leading to symptoms including hearing loss, tinnitus, and recurrent middle ear effusions. Despite bilateral grommet insertion for otitis media with effusion the symptoms persisted. An MRI, performed as part of further investigation, incidentally identified a 21x25x29 mm expansile mass in the left frontal sinus. The mass exhibited bony remodeling and extended into the ethmoid sinus, though visual disturbances were not observed. Endoscopic biopsy findings were consistent with JPOF. Management and Outcome: The patient underwent endoscopic resection, with histopathological analysis confirming juvenile psammomatoid ossifying fibroma. The case was reviewed at the National Sarcoma multidisciplinary meeting (MDM), where external craniofacial radical resection with immediate reconstruction was recommended to achieve complete resection and reduce the risk of recurrence. Discussion: This case illustrates the diagnostic challenges posed by JPOF, especially with its nonspecific symptoms and incidental discovery on imaging, as in this case. Persistent symptoms despite standard interventions prompted further investigation, ultimately leading to diagnosis. Histopathological confirmation was critical, and the management plan was refined through multidisciplinary collaboration. Conclusion: Juvenile psammomatoid ossifying fibroma may present with atypical symptoms and incidental findings, necessitating a high index of suspicion and comprehensive evaluation. This case underscores the importance of imaging, histopathological diagnosis, and a multidisciplinary approach in managing rare craniofacial tumors effectively.