Dilated odontoma is the most extreme form of dens invaginatus. The lesion appears as a roughly spherical mass that does not resemble a tooth but in a way appears tooth - like on radiographs due to somewhat similar radiodensity. The lesion is mostly spherical in appearance and hence the term "dilated." Occasionally, we come across cases of simultaneous pathologies. Here, we report two cases of a dilated odontoma one of which is associated with dentigerous cyst and in other case dilated odontoma pushing the maxillary sinus superiorly. Histologically, the mass was composed of dentinal tubules. These morphological and histological features are compatible with those of a dilated odontoma.