Odontogenic tumors are slow-growing and generally nonaggressive; however, aggressive characteristics appear to exist in particular tumors. The author reports two cases of benign odontogenic lesions at the anterior maxilla. A 44-year-old woman came to an oral-maxillofacial surgeon with a complaint of asymptomatic swelling of the left anterior region of the maxilla 15 years ago, which started gently but gradually increased over time. The patient experienced a physical injury 15 years ago, resulting in the loss of the upper left front teeth. In the other case, a 50-year-old woman complained for 5 years about a little swelling in her left anterior maxilla that became larger over time without causing any discomfort or pain. The Cone-beam computed tomography (CBCT) exam revealed a partially multilocular radiopaque mixed radiolucent lesion in the anterior maxilla, with margins that are both well-defined and ill-defined. Both display features of infiltrative, expansive, and moderately aggressive growths, leading to the erosion and perforation of the cortical plates in the buccal and palatal regions. Based on the biopsy results, both samples showed similar findings, specifically a benign odontogenic lesion, likely desmoplastic ameloblastoma, and squamous odontogenic tumor without any atypic cells or malignancy. This study aims to further our understanding of the clinical and radiological features of these patients and emphasize the importance of investigating specific lesions as potential diagnoses.