Dentigerous cysts are the most common developmental odontogenic cysts of the jaw, arising from impacted, embedded, or unerupted teeth. The majority of dentigerous cyst cases are single lesions. Bilateral and multiple cysts are very rare and generally occur in association with syndromes. In the present report, an unusual presentation of multiple dentigerous cysts that occupied four quadrants of dysplasia in a 45-year-old male was demonstrated by panoramic radiography and cone-beam computed tomography. The differential diagnosis, treatment, and imaging modalities are discussed after the case presentation together with a literature review from 1844 to 2013.