Odontogenic cysts and osseous lesions are often seen as challenging diagnostic lesions but the majority of them are easily classified. This article outlines the diagnostic features required for separating the most common of odontogenic cysts and select osseous lesions of the jaws. Clinical and radiographic findings of these jaw lesions often lead to a differential diagnosis that only the histologic findings will clarify. Dentigerous cyst, keratocystic odontogenic tumor, and certain ameloblastomas that have cystic change, may have identical radiographic findings, with only separation by their specific histologic features leading to the significantly different treatments required for each. Conversely, some cystic lesions can appear histologically identical and cannot be diagnosed without the radiographic findings. Certain osseous lesions of the jaws are particularly problematic for diagnosis without the appropriate radiographic findings, and the diagnosis should probably not be attempted on the histologic findings alone. This article will integrate the necessary clinical, radiographic, and histologic findings required to address the most common odontogenic lesions.