Orthokeratinized odontogenic cyst (OOC) is an uncommon developmental cyst of the jaws that usually occur singly, as a unilocular radiolucency affecting the posterior mandible of males. Bilateral OCCs are exceedingly rare, with less than 10 cases reported in the literature. Our study presents two new cases of bilateral OOCs. The first patient was an 18-year-old man who presented two bilateral well-circumscribed unilocular radiolucent lesions in the posterior mandible. The second patient was a 29-year-old woman with bilateral well-circumscribed unilocular (left) and multilocular (right) radiolucent lesions, located in the posterior mandible. The unilocular lesions were associated with unerupted lower molars. Microscopically, the cysts were entirely lined by orthokeratinized stratified squamous epithelium, confirming the diagnosis of OOC. Both patients were treated conservatively, and to date, no recurrence was evident. Clinicians should consider OOC during the evaluation of bilateral pericoronal radiolucent lesions in the posterior mandible of young adults. Orthokeratinized odontogenic cyst (OOC) is an uncommon developmental cyst of the jaws that usually occur singly, as a unilocular radiolucency affecting the posterior mandible of males. Bilateral OCCs are exceedingly rare, with less than 10 cases reported in the literature. Our study presents two new cases of bilateral OOCs. The first patient was an 18-year-old man who presented two bilateral well-circumscribed unilocular radiolucent lesions in the posterior mandible. The second patient was a 29-year-old woman with bilateral well-circumscribed unilocular (left) and multilocular (right) radiolucent lesions, located in the posterior mandible. The unilocular lesions were associated with unerupted lower molars. Microscopically, the cysts were entirely lined by orthokeratinized stratified squamous epithelium, confirming the diagnosis of OOC. Both patients were treated conservatively, and to date, no recurrence was evident. Clinicians should consider OOC during the evaluation of bilateral pericoronal radiolucent lesions in the posterior mandible of young adults.