Background: Broad ligament fibroids are rare extrauterine leiomyomas that can mimic adnexal or retroperitoneal masses, often leading to diagnostic and surgical challenges. Case Presentation: We report two cases of broad ligament fibroids with distinct presentations. The first case involved a 42-year-old woman presenting with abdominal distension and a mass equivalent to 34 weeks’ gestation. Imaging suggested a retroperitoneal or uterine mass; surgical exploration revealed a large right-sided broad ligament fibroid with cystic degeneration. The second case was a 70-year-old woman with anorexia, weakness, and renal dysfunction. Imaging showed a pelvic mass with mild left hydronephrosis. Surgical removal and histopathology confirmed a broad ligament fibroid with hyaline degeneration. Conclusion: These cases highlight the diagnostic complexities of broad ligament fibroids, in differentiating them from ovarian or malignant pelvic masses. Early surgical intervention remains the definitive treatment, with intraoperative care essential to avoid injury to adjacent structures and to confirm diagnosis via histopathology.