Background: Leiomyomas are usually easily identifiable on routine imaging. However, there is increasing difficulty with diagnosing leiomyomas following degeneration. Subserosal leiomyomas that undergo cystic degeneration can imitate ovarian pathology. Case: We present the case of a 39-year-old nulligravid woman who underwent surgery for a large pelvic mass originally suspected to be of ovarian origin. Intraoperatively, the mass was found to originate from the uterus and determined to be a large pedunculated, fluid-filled cyst arising from a fibroid which had undergone cystic degeneration. The mass was successfully removed laparoscopically through a single, two-centimeter port. Conclusion: Gynecologists and radiologists should take into account this presentation when encountering suspected enlarged ovarian cysts without clearly identifying an origin. Laparoscopic intervention should be considered as the first line of management.