This research aims to correlate drivers’ characteristics with their safety performance. In order to achieve this objective, two different data sets were used deriving from 12 drivers who participated on an on-road driving experiment while being assessed by a safety behaviour expert. Drivers participating in the experiment also responded to the questionnaire administered, which mainly included self-evaluation questions along with other that concerned the condition of their vehicle, demographics, driving experience etc. The analysis of drivers’ behavior was carried out using the statistical methods of factor analysis and linear regression analysis. Three groups that characterize drivers’ perception of careless, aggressive and cautious driving behavior were derived from factor analysis. Moreover, linear regression analysis revealed that driving experience, headways, self-reported driving skill and defensive driving positively affect the overall on-road driving performance score. More precisely, it was ascertained that driving experience leads to statistically significant increase in overall on-road driving performance score. Other factors such as defensive driving and keeping safe distances from other vehicles. The findings of this research could be exploited for providing feedback on drivers regarding their driving behavior in order to further reduce their driving risk.