This study is the first examination on the association between seven types of sleep disorder and driving risk using large-scale naturalistic driving study data involving more than 3,400 participants. Regression analyses revealed that females with restless leg syndrome or sleep apnea and drivers with insomnia, shift work sleep disorder, or periodic limb movement disorder are associated with significantly higher driving risk than other drivers without those conditons. Furthermore, despite a small number of observations, there is a strong indication of increased risk for narcoleptic drivers. The findings confirmed results from simulator and epidemiological studies that the driving risk increases amongst people with certain types of sleep disorders. However, this study did not yield evidence in naturalistic driving settings to confirm significantly increased driving risk associated with migraine in prior research. The inconsistency may be an indication that the significant decline in cognitive performance among drivers with sleep disorders observed in laboratory settings may not nessarily translate to an increase in actual driving risk. Further research is necessary to define how to incentivize drivers with specific sleep disorders to balance road safety and personal mobility.