Background Commercial vehicle accidents are the leading cause of occupational fatalities and an increased risk of traffic accidents is associated with excessive fatigue, other health problems as well as poor sleep during work. This study explores individual and occupational factors associated with different levels of daytime sleepiness and identifies their association with driving risk among occupational drivers working at construction sites. Methods This cross-sectional and correlational study adopted a self-reported questionnaire of Korean construction drivers (N = 492). The data were collected from October 2018 to February 2019 using a battery of six validated instruments about participants’ sociodemographic, health-related, and occupational characteristics. One-way ANOVA and multinomial logistic regression were conducted using IBM SPSS WIN/VER 25.0, with a two-tailed alpha of .05. Results Based on the Epworth Sleepiness Scale, “moderate” (31.7%) and “severe” (10.2%) daytime sleepiness groups were identified. There were significant differences in break time, driving fatigue, depressive symptom, subjective sleep quality, physical and mental health, and driving risk among the three groups (all p-values < .001). Driving fatigue (Adjusted Odds Ratio [aOR] = 1.08, 1.17), depressive symptoms (aOR = 0.91, 0.98), subjective sleep quality (aOR = 1.18 in moderate only), and driving over the speed limit (aOR = 1.43, 2.25) were significant factors for determining “moderate” and “severe” daytime sleepiness groups, respectively. Conclusion A significant number of construction drivers experience excessive daytime sleepiness; thus it is important to reduce the negative impact of driving fatigue and other factors on daytime sleepiness. Our study findings suggest that occupational health care providers should pay attention to development and implementation of health management interventions to reduce driving fatigue that incorporate the drivers’ physical, mental, and occupational factors. Professional organizations need to establish internal regulations and public policies to promote health and safety among occupational drivers who specifically work at construction sites.