Background: Driving cessation is strongly associated with adverse health outcomes in the older adults. Although there were numerous documentations of driving rehabilitation in disabled adults, the effects of interventions on safe driving were not clear in older adults with cognitive impairment who had low driving skills. Objective: This randomized controlled trial was designed to determine whether a safe driving skill program consisting of classroom and on-road training could enhance driving performance of older drivers with cognitive impairment in Japan. Methods: A total of 160 community-living older drivers participated in the randomized controlled trial with blinded endpoint assessment. Participants randomized to intervention underwent 10 1-h classroom sessions and 10 1-h on-road sessions focused on common problem areas of older drivers. Controls received 1 classroom education. On-road driving performance was assessed by certified driving school instructors in a driving school. The participants carried out dynamic vision and cognitive performance tests. Results: One hundred and forty-six (intervention group, n = 71) subjects completed the 3-month follow-up. Mean adherence to classroom-based vision training and driving simulator training and on-road training programs, including the 71 participants, was 99.0 ± 6.4 and 99.0 ± 7.2%, respectively. Regarding the safe driving skill score, there were group × time interactions (p < 0.01) indicating benefits of the intervention over time. Although there were no significant group × time interactions in cognitive tests, dynamic vision showed group × time interactions (p < 0.01). Conclusion: The driving skill program significantly improved safe driving performance in older adults with cognitive impairment who were at a potentially high risk of a car accident.