Narratives of ageing are often negative, focusing on later life as a period defined by biological decline. A growing population of older adults (Masters athletes) participating in sport challenge these assumptions. Existing research demonstrates how Masters athletes transcend and challenge dominant discourses of ageing and resist enfeeblement. To do so requires a negotiation with risk, pain and injury. Examining these processes in younger athletes developed within the sociology of sport during the 1990’s. This literature explored risk-taking sub-cultures across different sports and between genders. Yet An analysis of how older athletes manage risk has hitherto not taken place. In order to expand this corpus of work to Masters athletes, this article provides a case study of the Masters Highland Games. Drawing upon in-depth interviews with 19 athletes aged between 40 and 75, two ideal types that describe approaches to risk taking are proposed. Informed by the ideas of Giddens, these ideal types will demonstrate the variety of ways that resistance relates to risk, pain and injury. This case study demonstrates that some Masters athletes share traits identified in research with younger athletes, such as the acceptance of their practice being inherently risky and the act of normalising pain. However, most Masters athletes exhibit a more problem solving approach that adopts various strategies that manage the risks of ageing.