Background: Dentigerous cyst is one of the most common developmental odontogenic cysts and is characteristically associated with the crown of an unerupted or impacted tooth. Although frequently encountered in the posterior mandible, unusual presentations involving the mandibular anterior and premolar region may create diagnostic challenges.

Case Report: A 23-year-old male reported to the Department of Oral and Maxillofacial Surgery with pain and swelling in the lower left posterior tooth region for approximately 15–20 days. Medical and personal histories were non-contributory. Clinical examination was supplemented by panoramic and cross-sectional radiographic investigations, which demonstrated a radiolucent lesion involving the mandibular left anterior–premolar region. A provisional diagnosis of an odontogenic cyst was considered. Fine-needle aspiration cytology revealed inflammatory cells, macrophages and debris and was reported as suggestive of an inflammatory lesion. Surgical management was performed under local anesthesia. Extraction of teeth 75, 34 and 35 was followed by surgical enucleation of the cystic lesion. The excised tissue was submitted for histopathological examination. Histopathological examination demonstrated a cystic lumen lined by epithelium with an underlying connective tissue stroma, confirming the diagnosis of a dentigerous cyst. Postoperative healing was satisfactory, with progressive resolution of the surgical site at subsequent follow-up visits.