The experiences of women in sport continue to necessitate deliberation, reflection, new ways of thinking, and further discourse in the continued pursuit of opportunity and equality. The subsequent and parallel impact on the roles that women play in sport as athletes and leaders are revealed by identifying the complexities and social realities that are vying and contending for relevance. The notion of complexity offers a novel conceptualization revealing contexts and competing points of view that challenge progress and equality for women in sport. Complexity refers to the state of the world assailed by increased amounts of data, facts, tasks, evidence, and arguments that yield uncertainty in the current age and unpredictability for the future. Universal challenges characteristic of complexity include globalization; digital technology; interpenetration of the wider society; participation, access, and equal opportunity; marketization; competition; and quality assurance and assessment. As a result, these old and new realities raise questions related to what we know about the current state of sport, sport experiences of women, and the properties of sport that seem difficult to manage. The purpose of this paper is to offer complexity as a theoretical lens by which to examine sport, discuss the universal and formidable challenges that face sport, and, more specifically, discuss the impact they have on women in sport.