In much of his work, H. G. Wells consciously criticises the conservativeness of contemporary sports such as cricket and emphasises cycling as a recreational sport which contributes to the democratisation of social class and gender. This stance is apparent in Wells's first social novel, The Wheels of Chance (1896) which captures the fin-de-siècle passion for cycling but also its social impact. For Wells, Victorian team/spectacle sports such as rugby, football, horseracing, and boxing are overtly competitive, promoting gentlemen's amateur sportsmanship and masculinity. This essay argues that The Wheels of Chance, by featuring recreational cycling as the main motif and casting an unfit draper as the protagonist, is an indirect criticism of gentlemen's sporting activities. It creates a space of amusement where strict rules are shunned in favour of casual pastime, generating carnivalesque games and performances in the Bakhtinian sense. It explores the author's will to change the social order through the carnivalesque, in the ambivalent depiction of Mr Hoopdriver's bi-cycling as play.