Ovarian cysts are a common gynecologic finding in adolescent females and are typically benign, often resolving without requiring intervention. However, larger cysts can cause significant symptoms and pose a risk for complications such as torsion. These cysts were traditionally removed with a full midline laparotomy. Surgery as a field has moved towards minimally invasive approaches to promote healing and aesthetics. With large benign cysts, this is achieved with controlled intentional decompression, allowing for extraction with a smaller incision. In this case, we present a 14-year-old female who presented with abdominal discomfort and was found to have a 24x20x9-cm left ovarian cyst. She underwent controlled cyst decompression into a specimen bag, minimizing peritoneal contamination prior to removal of the cyst. This was achieved in a 5-cm Pfannenstiel incision. The patient was discharged the same day without complications and demonstrated full recovery with no cyst recurrence at the 12-week follow up. This case highlights the safe, effective management of large benign ovarian cysts using controlled decompression and innovative containment strategies to enable minimally invasive surgical access.