Squamous cell carcinoma is defined as an invasive epithelial neoplasm, with variable degrees of squamous differentiation, with or without keratinization. It is origins stand at the level of the keratinized stratified squamous epithelium (skin) or non-keratinized (oral mucosa, esophageal mucosa, uterine exocervical mucosa), but it can also be found in squamous metaplasia areas (uterine endocervix or trachea-bronchial tree). This report presents the case of an oral squamous cell carcinoma as a second malignancy in the same anatomical territory, in a patient with prior treatment for chondrosarcoma, both surgical and radiotherapy. The tumor had appeared 5-6 months prior and had undergone a relatively rapid growth, this being the patient's main motive for addressing the doctors. The tumor was greyish, with imprecisely demarcated margins, of firm consistency, bleeding and with local necrotic deposits. The tumor extended from the incisive region to the maxillary tuberosity, towards the cheek mucosa and the soft palate. After a large excision, the histopathological diagnosis was infiltrative keratinizing squamous cell carcinoma, with moderate differentiation, with origins in the oral mucosa, infiltrating the whole of the maxilla and the maxillary sinus mucosa. Approximately three months after the surgery, a new tumor appeared in the oral cavity, on superior and inferior mucosa of the right cheek, extending towards the right buccal commissure, implying a relapse of the primary tumor. Postoperative oncological therapy included standard chemotherapy, which resulted in favorable postoperative evolution. This case is interesting by the association, of two metachronous malignant tumors, of different histological origin: a chondrosarcoma and a squamous cell carcinoma, at an interval of 25 years.