The thesis explores the early history of bicycle racing in New Zealand, from its introduction in 1869, until the major decline of public interest in bicycle racing on specially constructed oval tracks which was, practically speaking, complete by 1910. Particular attention will be paid to the development of “cash amateur” bicycle racing, which began in Melbourne in 1890, before spreading to New Zealand in 1892. The position will be taken that sport is socially constructed and that the institutions which are grown around it are shaped by, and reflect, broader cultural, political and social norms. It will, therefore, examine the social construction and meaning of the terms “amateur”, “cash amateur” and “professional”. It will contend that while athletes were classified by such behaviours as the acceptance of cash prizes or membership of governing bodies, concepts of race, sex, and class also informed descriptions of these behaviours by stakeholders in the construction process such as the press, bicycle manufacturers, promoters of bicycle racing and by the bicycle racers themselves Focus will be placed on bicycle racing in New Zealand, with comparative reference to Australia, Britain, the United States and Continental Europe (primarily France). A central premise of this thesis is that nineteenth century New Zealand society was highly interconnected with a wider Anglophonic cultural, political and economic world, and that industrialised communication – steam ships, railways and telegraph – enabled and hastened the diffusion of trans-national cultural phenomena such as “velocipede mania” and the “bicycle boom”. Within these broader movements there was, however, room for localised variations. Cash amateurism, it will be argued, was one such local solution to the problem of reconciling the ideologies of amateurism and laissez-faire capitalism, the divergence of which was sharply identifiable in bicycle racing. The overarching thesis is thus one of social and cultural history, exploring the social and institutional organisation of bicycle racing within a broader social and cultural context. It is structured as a narrative with chronological organisation. Within this framework, it explores themes of class, race, sex and identity, amateurism, professionalism and commercialism in sport, cultural construction by the press and modernity as a commercialised commodity.