Dentigerous cysts are thought to be caused by a developmental abnormality derived from the reduced enamel epithelium of the tooth forming organ. Most typical dentigerous cysts are those associated with the third molar teeth of the mandible, but rarely involve impacted supernumerary teeth in the anterior maxilla. Swelling and/or pain may be the major complaints of the patients. Herein, we review the literature spanning the past 22 years concerning dentigerous cysts associated with supernumerary teeth in the anterior maxilla, and present four additional cases with emphasis given to the clinicopathological characteristics of this type of dentigerous cyst.