A Diploma Thesis titled “Correlation of driver characteristics and its safety performance” was presented by Vasiliki Agathangelou in July 2016, with the support and data from OSeven Telematics. Data from an experiment on driver behaviour assessment from an expert was exploited, using on-road driving in conjunction with a self-evaluation questionnaire. The analysis of the drivers’ behaviour was carried out through factor and linear regression analyses. Three groups that characterise drivers’ perception of careless, aggressive and cautious driving behaviour were derived from factor analysis. Moreover, linear regression analysis revealed that driving experience, headways, self-reported driving skills and defensive driving affect positively the overall on-road driving performance score. It was ascertained that driving experience leads to statistically significant increase in overall on-road driving performance score.