This paper offers a microstudy, deconstructing the meaning and significance of a famous carriage (or chaise) match at Newmarket in 1750 and a contemporary painting of the event. It uses these as a starting point to explore its relationship to debates about the early modern period and modernity. It analyzes the details of the carriage match, exploring its visual and print representations and its cultural context. It further argues that, for many sports at this time, the development of more formal regulations was driven by gambling and that gambling’s centrality needs to be recognized better. It then analyzes the event’s relationship to modernity issues such as scientific rationality, quantification, record keeping, and emerging bureaucratization. Finally, the essay shows how, rather than being mere servants or grooms, at least some of those involved were able to achieve high levels of wealth and status. This suggests that mid-eighteenth-century England had already moved toward further modernity in sports such as racing than has been assumed.