Background <p>Benign fibro-osseous lesions (BFOLs) of the jaws are characterized by the replacement of normal bone with fibrocellular stroma and mineralized material, including bone and cementum-like tissue. Their overlapping radiological and histopathological features often present diagnostic challenges. Recent WHO classifications have refined their categorization, highlighting the importance of distinguishing cemento-ossifying fibroma (COF), juvenile trabecular ossifying fibroma (JTOF), and psammomatoid ossifying fibroma (PsOF).</p> Methods <p>A retrospective analysis of 24 cases (7 COF, 6 JTOF, 11 PsOF) diagnosed between 2020 and 2023 was conducted at a tertiary care center. Clinical, radiological, and histopathological data were reviewed by a multidisciplinary team. Radiographic patterns, histological features, and clinical outcomes were compared among the three entities.</p> Results <p>COF predominantly affected adult females, presented mainly in the mandible, and showed a mixed radiolucent–radiopaque pattern with cementum-like calcifications. JTOF and PsOF occurred in younger patients, exhibited more aggressive behavior, and showed a male predominance in PsOF. JTOF presented with osteoid trabeculae lined by osteoblasts, while PsOF was characterized by psammomatoid bodies with osteoid rims and delicate, wispy eosinophilic collagen fibers at the periphery lacking osteoblastic rimming. Recurrence was not observed in any case during 4–56 months of follow-up following surgical treatment, which included enucleation with peripheral osteotomy or resection.</p> Conclusion <p>COF, JTOF, and PsOF display distinct demographic, anatomical, and microscopic characteristics despite overlapping features. Accurate differentiation, aided by updated WHO classifications, is critical for optimal management. Recognizing these distinctions allows for appropriate surgical planning, reduces misdiagnosis, and prevents overtreatment.</p>