Multiple primary malignancies are not rare. While metachronous triple cancers are rare and a triple tumor case involving maxillary sinus and tympanic membrane is exceptionally rare. We present such an extremely rare case with the index tumor of adenoid cystic carcinoma of the maxillary sinus and 14 years later esophageal cancer was observed as a metachronous tumor. One year after esophageal cancer, squamous cell carcinoma arising from tympanic membrane was detected. Before the tumor of tympanic membrane was observed, the patient had received total three radiation courses. Prior radiation therapy is suspected to be playing a role in inducing the squamous cell carcinoma of the tympanic membrane.