Odontomas and dentigerous cysts are common findings for practicing dental professionals. However, simultaneous occurrence of pathologies like odontoma and dentigerous cyst are uncommon and their diagnosis based on the radiographic appearance alone is a challenge to overcome. They together are a potential for complications like attaining large size, root resorption, destruction of the jaw bones and sometimes neoplastic changes like ameloblastoma. This paper presents a case of complex odontoma associated with dentigerous cyst in relation to a retained deciduous tooth in the maxillary anterior region and confirming its diagnosis histopathologically.