Uterine leiomyomas are one of the most common reproductive pathologies in born females. The majority of women within reproductive age will develop a leiomyoma, most of which will be asymptomatic. Though there has been extensive research regarding this pathology alone, there is more to be learned about leiomyomas that affect women with other comorbidities. This case study reviews the medical and surgical management of a woman born with two uteri, medically termed congenital uterus didelphys. Within her reproductive years, she develops symptomatic leiomyomas in each of her uteri and seeks surgical management. This case study aims to widen the scientific knowledge surrounding these subsets of women with a common diagnosis superimposed on an extremely rare diagnosis.