Dentigerous cysts are developmental odontogenic cysts associated with the crown of an unerupted tooth most commonly located at permanent Mandibular 3rd Molars and the Maxillary Canines. They rarely involve deciduous teeth and supernumerary teeth [5%]. We report successful management of two rare cases of maxillary labial swelling due to a dentigerous cyst associated with an impacted mesiodens. This paper highlights unusual occurrence of dentigerous cyst in anterior maxilla associated with impacted supernumerary teeth, which was surgically enucleated along with involved tooth. Key to successful treatment is careful evaluation of patient history, establishment of clinical and radiological findings, early diagnosis and surgical management to prevent future complications.