Diffuse idiopathic skeletal hyperostosis (DISH) is characterized by the calcification and ossification of ligaments and tendons. Progressive dysphagia caused by DISH-related anterior cervical osteophytes and deteriorating dysphagia caused by DISH combined with neurological dysfunction resulting from the posterior longitudinal ligament is rare. The initial diagnosis is misleading and patients often consult several specialists before spine surgeons. This study aims to provide a comprehensive review of the literature on this challenging pathological association. We also present a case illustration where a 53-year-old man presented with progressive dysphagia and foreign body sensation in the pharynx, accompanied by a neurological numbness defect in the right upper limb. Radiography and computed tomography confirmed the existence of osteophytes at the anterior edge of the C4-C7 pyramid and ossification of the posterior longitudinal ligament, in which the giant coracoid osteophyte could be seen at the anterior edge of the C4-C5 pyramid. The anterior cervical osteophyte was removed, and decompression and fusion were performed. The symptoms were relieved postoperatively. No recurrence of symptoms was found during the six-month follow-up. Spine surgeons should consider progressive dysphagia caused by DISH-related osteophytes at the anterior edge of the cervical spine as it is easily misdiagnosed and often missed on the first evaluation. When combined with ossification of the posterior longitudinal ligament, following cervical osteophyte resection it is necessary to consider stabilizing the corresponding segments via fusion.