Background Insufficient sleep is a common health and safety risk factor in high-impact workplaces where workers are required to take rotating shifts. However, studies on sleepiness-related risks and incidents, particularly among emergency medical services (EMS) workers are limited. Objective This study sought to investigate the prevalence of sleepiness and related workplace incidents among EMS workers. Methods This study utilized a cross-sectional survey design on a convenient sample of 500 EMS workers from 41 EMS squads across Taiwan. Data were collected using structured online questionnaires on workplace sleepiness and related safety incidents based on the Epworth Sleepiness Scale (ESS) and a modified 25-item EMS Safety Inventory respectively. Results With a response rate of 79.8% (n = 399), 36.9% of the respondents were identified as having mild daytime sleepiness, while 39.2% of the respondents were identified as having excessive daytime sleepiness. Multivariate analysis indicated that not only was working on rotating shifts the main cause of the high ESS scores among EMS workers, but also that higher ESS scores increased their risk of sustaining a workplace injury. Furthermore, ill-at-work incidents were associated with an increased risk of workplace-related injuries. Conclusion Overall, the findings indicated a correlation among working on rotation shifts, the prevalence of sleepiness, and a higher risk of workplace injury among EMS workers.