The purpose of this study was to clarify the characteristics of fair play in the pre-modern era, targeting pugilism in the 18^th century, by focusing on the essence of gambling-oriented spectator sports. Specifically, this study employed the following processes. First, it analyzed the practice of gambling-oriented spectator sports from the perspective of the concept of figuration, and clarified the process of development of order (rules) in spectator sports as well as the characteristics of fair play. Second, it analyzed Broughton's Rules of pugilism from a figuration perspective to identify their function and the characteristics of fair play reflected in them. Third, it examined the process by which fair play was transformed during the transition from the pre-modern to the modern era by exploring the impact of the revision of Broughton's Rules as the London Prize Ring Rules. The following findings were established. First, the main function of Broughton's Rules was not to promote a moral attitude, but rather to guarantee interesting bouts and the viability of gambling. The fair play in spectator sports conducted in accordance with these rules manifested itself in the “performance” of a bout that, fought skillfully and carefully right to the end, embodied the qualities of manliness, courage, and endurance while being free of unnecessary accidents and injuries. Second, in the 18^th and early 19^th centuries, amid changes in the interpersonal networks connecting the people involved in gambling-oriented spectator sports, fair play in pugilism evolved under the influence of an emphasis on greater clarity. As a result, conduct that had previously been permitted came to be prohibited under the London Prize Ring Rules. The present findings clarified that standards used for judging the fairness and desirability of conduct fluctuated in accordance with changes in interpersonal networks.