The buccal bifurcation cyst (BBC) is an uncommon odontogenic inflammatory cyst affecting the vestibular aspects of the first or second mandibular molar of pediatric patients. Its etiopathogenesis is not fully understood, but it is hypothesized that food and detritus impacting buccal periodontal pockets in titled tooth would be responsible for inflammation of the pericoronal tissues, leading to proliferation of epithelial rests and subsequent cystic formation. The true prevalence of the BBC is not known, but it is estimated to be less than 1% of all the inflammatory cysts. Most cases are unilateral but bilateral cases may account for up to 30% of all BBCs, which can generate confusion to unfamiliar clinicians. Maxillary cases are extremely uncommon, and to our knowledge, there are no cases published in the English literature. In this case series, we present five BBC cases; two unilateral, two bilateral, and one affecting the maxilla. We included clinical, imaging, and histopathological information to highlight the different presentations that this cyst might have, with the final aim to aid clinicians in its diagnosis and ultimately, its treatment.