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Plummer–Vinson syndrome is known as the association of dysphagia, upper esophageal web, weight loss, and iron-deficiency anemia. Esophageal dilation therapy is usually necessary to remove webs and to relieve dysphagia in order to encourage oral intake. We report two cases of Plummer–Vinson syndrome. Both patients presented with significant and longstanding dysphagia, sideropenia, and painful swallowing. Patients’ esophagograms revealed the presence of tight stenosis in the high cervical esophagus. Both patients were treated with fluoroscopically guided balloon dilation and iron supplementation. These patients were followed up after the initial treatment and showed improvement of dysphagia and iron-deficiency anemia.