This article provides an investigation into masculinities amongst competitive male road cyclists. The paper reports on a quantitative study, involving a self-report survey which was distributed to a male population of UK competitive road cyclists (n = 105). Results indicate the sample more closely identify with an explicit notion of masculinity than seen in the general male population, and this finding was consistent across age groups. The study explores the importance of these findings with Inclusive Masculinity Theory, suggesting that competitive road cycling presents a cultural lag relative to wider societal changes in masculinity. Implications for participation in the sport, risk-taking, and concussion, as well as sexual diversity support, are discussed.