Carcinoma of the oral cavity sometimes metastasizes to the lateral retropharyngeal lymph node (LRPLN), especially when posteriorly invading the soft palate or oropharynx. CT or MRI imaging has enabled detection of LRPLN metastasis in the early stage, but the prognosis of patients with metastasis to this node is extremely poor. The authors report three patients with squamous cell carcinoma of the oral cavity with no posterior invasion who developed metastasis to LRPLN during observation. The primary sites of these three cases were gingiva of the upper incisor region, gingiva of the lower premolar region, and maxillary bone of the upper incisor region. Each patient underwent surgery as their initial therapy, but a recurrent tumor in the LRPLN was detected by CT or MRI despite good loco-regional control. A salvage operation with postoperative radiation therapy was performed for two patients, but only one is still alive with no evidence of tumor 14 months after the last surgery. Management of LRPLN metastasis in oral cancer patients is a challenge for oral surgeons, but early detection by CT or MRI and surgery with postoperative radiation therapy is likely to yield the best local control.