Driving is a highly complex task requiring multiple cognitive processes that can be adversely affected post-stroke. It is unclear how much ability post-stroke adults have to self-evaluate their driving performance. Furthermore, the impact of cognitive decline on this evaluation has not been previously investigated. The aim of this study was to investigate the perceived level of task demand involved in driving tasks, and to examine differences between perceived and observed driving performance in post-stroke drivers in comparison to a control group. A further aim of the research was to investigate the influence of cognition on self-rated driving performance. A total of 78 participants (35 post-stroke and 43 controls) were assessed using a series of cognitive tasks and were observed whilst driving. Participants were asked to rate their own driving performance and the task demand involved while driving using the NASA Task Load Index. Between group analyses were conducted to determine differences in the level of self-rated performance and task demand. Further analyses were conducted to investigate whether cognition accounted for differences in task demand or self-rated performance. Overall, the results suggested that the post-stroke drivers exhibited deficits in cognition, but they did not report increased levels of task demand when driving. Post-stroke adults also rated themselves more conservatively than the controls for on-road performance, which was associated with their reduced propensity for risk. The study suggests that cognitive deficits may influence post-stroke drivers to amend their driving behaviour, in order to bring the task demand within a manageable level. Understanding the mechanisms involved in self-rated performance and estimations of task demand can help promote accurate self-regulation practices in post-stroke drivers. Furthermore, measuring calibration may assist practitioners with assessing fitness-to-drive, as well as with tailoring driving rehabilitation.