Introduction: A dentigerous cyst is a developmental cyst of odontogenic origin, which apparently develops by accumulation of fluid between the reduced enamel epithelium and the tooth crown of an unerupted tooth, with consequent expansion of tooth follicle. It may be associated with crown of unerupted teeth, odontomas, or supernumerary teeth. Ninetyfive percent of dentigerous cysts are associated with permanent dentition whereas only 5% are with supernumerary teeth. Case Report: Herein, we report a case of dentigerous cyst associated with impacted inverted supernumerary tooth in anterior maxilla in a 28-year-old male. The patient was treated surgically by enucleation of total cyst and surgical extraction of mesiodens under local anesthesia and was subsequently confirmed histopathologically. Conclusion: Recurrence of dentigerous cyst is rare and could be due to the residual fragments of the cystic lining. To prevent the development of a dentigerous cyst and to avoid unwanted effects on adjacent teeth, early detection consisting of a through clinical and radiographic examination is necessary for accurate diagnosis and proper treatment planning.