The uterus is a multifunctional organ central to both reproductive and nonreproductive health. The contractility of its muscular wall, the myometrium, is a tightly regulated process, dynamically adapting across the menstrual cycle, pregnancy, labor, and postpartum periods. Dysfunctional myometrial contractility underlies significant clinical issues including dysmenorrhea, infertility, preterm birth, labor arrest, and postpartum hemorrhage. Understanding its function requires an appreciation for its intricate cellular and structural basis, multilayered regulation and nuanced contractile functions. This chapter discusses the central importance of myometrial contractility, providing biological context important for its investigation through bioengineering approaches. It also provides an overview of early and advanced bioengineering methods used to replicate or investigate myometrial contractility, identifying opportunities for future advancements in this field.