Purpose. We present a case of a bilateral postoperative maxillary cyst (PMC) and discuss this with a systemic review. Case Report and Literature Review. A 68-year-old female with pain and swelling on the right side of the face. MRI and CT showed a cystic tumors of the right and left maxillary sinus. Radical maxillary surgery via a Caldwell-Luc procedure had been performed 55 years ago and bilateral PMC was diagnosed. The PubMed database was searched for PMC within the last 30 years. Results. Together with the current case, we found 23 reports including 284 patients describing PMC. It was diagnosed at a mean time of 22 years after causal surgery at a mean age of 47 years. Initial symptoms were mostly pain with or without swelling. The main radiological sign was a unilocular radiolucency with a slight preference for the left side. Discussion. PMC is a long-term complication that can occur after maxillary sinus surgery and a second surgical approach is required in order to stop cystic expansion. Therefore, patients' informed consent on this complication as well as a prolonged follow-up is recommended. Simple paranasal ultrasound or paranasal sinus plain radiography may lead to an earlier detection reducing interventional morbidity.