Sleepiness is a significant contributor to car crashes and sleepiness related crashes have higher mortality and morbidity than other crashes. Young adult drivers are at particular risk for sleepiness related car crashes. It has been suggested that this is because young adults are typically sleepier than older adults because of chronic sleep loss, and more often drive at times of increased risk of acute sleepiness. This prospective study aimed to determine the relationship between predicted and perceived sleepiness while driving in 47 young-adult drivers over a 4-week period. Sleepiness levels were predicted by a model incorporating known circadian and sleep factors influencing alertness, and compared to subjective ratings of sleepiness during 2518 driving episodes. Results suggested that young drivers frequently drive while at risk of crashing, at times of predicted sleepiness (>7% of episodes) and at times they felt themselves to be sleepy (>23% of episodes). A significant relationship was found between perceived and predicted estimates of sleepiness. However, the participants nonetheless drove at these times. The results of this study may help preventative programs to specifically target factors leading to increased sleepiness when driving (particularly time of day), and to focus interventions to stop young adults from driving when they feel sleepy.