Jaw pseudocysts are benign osseous lesions of unclear etiology. Among these, the simple bone cyst (SBC) and aneurysmal bone cyst (ABC) are intriguing bone pathologies still rarely studied together. This retrospective study aimed to present the long-term case series of patients with jaw pseudocysts focusing on the clinical, radiographic, and transoperative aspects. A retrospective case series of patients with SBC and ABC was performed. Clinical, radiographic, and transoperative aspects of both pseudocysts were reviewed from the histopathological archives of 20,469 cases between 1959-2012. All descriptive data were summarized. Of 354 (15.25%) bone pathologies, 54 cases of jaw pseudocysts were found, with 42 (11.86%) SBC and 12 (3.39%) ABC cases. For both lesions, most of the sample were young Caucasian women with an asymptomatic posterior mandible lesion with undetermined time of evolution and none trauma history. A unique radiolucent scalloped lesion presenting an empty cavity were also observed for both conditions. However, some atypical findings were found for SBC including: the expansion of bone cortical, tooth resorption, displacement of the mandibular canal, and recurrence. The absence of painful symptoms and the lack of classical blood-filled cavity were observed in some cases of ABC. The SBC and ABC are bone pathologies with few retrospective studies, no previous studies on the two conditions, varied nomenclature, and atypical aspects in some cases. Therefore, the knowledge of clinical, imaging, and transoperative features of such pseudocysts are clinically valuable as diagnosis hypothesis of radiolucent lesions of the jaws.