Olympic equestrian sport has to date evolved through three distinct phases of development. The genesis of equestrian sport in the modern Olympics began in 1900 and was predominantly shaped by military influences until 1948. Pre-1900 equestrian sport existed in various forms around the world primarily to develop and practice skills of hunting and warfare. At this time, equestrian sport lacked governance and internationally standardized rules. This paper’s aim is to explore the influence of the military on the first phase of equestrian sport development in the Olympic Games between 1900 and 1948 with regards to their format and rules. Through thematic analysis of the narratives evident in the literature, we highlight influential military developments/changes that occurred outside the confines of sport, and place the sociocultural development of equestrianism within this framework. This reconstructive approach has enabled us to highlight the relevance of the military influence on the development of equestrian sport. Through the identification and analysis of perceptions of Olympic equestrianism, which are centred upon the Eurocentric, military-influenced development of the sport, the paper also discusses implicit and explicit references to, and the relevance of, masculinity elitism and social class, along with issues of amateurism and professionalism.