The COVID-19 pandemic has taught us to live in social isolation and has brought an important element of social life, the events industry, to a complete standstill. In resurrecting the events industry, the most urgent focus is on managing the risk of any crowd-control measures with a view to reducing to zero the danger of the virus spreading. This research focuses on the main issue of the impact of the coronavirus disease 2019 (COVID-19) on the organization of sports events (SEs), and in particular, cycling competitions. This study, therefore, aims to provide deeper insights into (a) the measures introduced to face the health emergency situation in cycling events, (b) the comparison of these measures with previous experiences in similar SE contexts, and (c) the possible evolution of organizational models for cycling events in the post-pandemic era. Fifteen semi-structured interviews with cycling athletes, managers, and officials constitute the methodological basis for this study. The results show that countermeasures have been taken that are effective in dealing with pandemic characteristics and are likely to be applied in the future, while others will be phased out or used again only when necessary. This study enhances scientific knowledge by analyzing a renewed approach to risk management for SEs, with a specific focus on pandemics and medical risks. Finally, the study shows that cycling events need to adapt the specifics of such a new approach to the standards projected on future scenarios for which the COVID-19 pandemic has paved the way.