Cemento-Ossifying Fibroma (COF) is a rare benign tumor of the jaw characterized by the formation of cementum and bone-like tissue, often arising from the periodontal ligament. This article presents two clinical cases that illustrate the complexities of diagnosing and managing COF. The first case involves a 30-year-old male with a painless, progressively enlarging swelling in the left mandible, diagnosed through panoramic radiography and cone-beam computed tomography (CBCT). Surgical intervention included mandibular resection and reconstruction using an iliac graft. The second case features a 26-year-old female presenting with a non-painful swelling in the right mandibular premolar region, which was also confirmed via imaging studies. Complete surgical resection was performed, and histopathological examination validated the diagnosis of COF. Both cases highlight the importance of accurate diagnostic imaging and histological analysis in confirming COF, as well as the need for individualized surgical approaches based on lesion characteristics. Despite its benign nature, COF can lead to significant morbidity due to local invasion and recurrence potential. The article emphasizes that thorough follow-up is essential to monitor for recurrence after surgical management. These cases contribute to the understanding of COF's clinical presentation and reinforce the necessity for a multidisciplinary approach in managing this condition effectively. Further research is needed to explore the underlying pathogenesis and optimize treatment strategies for COF in clinical practice.