Most older adults perceive themselves as good drivers; however, their perception may not be accurate, and could negatively affect their driving safety. This study examined the accuracy of older drivers’ self-awareness of driving ability in their everyday driving environment by determining the concordance between the perceived (assessed by the Perceived Driving Ability [PDA] questionnaire) and actual (assessed by electronic Driving Observation Schedule [eDOS]) driving performance. One hundred and eight older drivers (male: 67.6%; age: mean = 80.6 years, standard deviation [SD] = 4.9 years) who participated in the study were classified into three groups: underestimation (19%), accurate estimation (29%), and overestimation (53%). Using the demographic and clinical functioning information collected in the Candrive annual assessments, an ordinal regression showed that two factors were related to the accuracy of self-awareness: older drivers with better visuo-motor processing speed measured by the Trail Making Test (TMT)-A and fewer self-reported comorbid conditions tended to overestimate their driving ability, and vice versa.