The aim of this Diploma Thesis is the comparative analysis of road safety factors across generations in Greece with the use of statistical models. To this end, appropriate data were collected concerning the characteristics of road crashes in Greece in the period between 1985 and 2018. Data analysis was conducted for each generation separately (Silent Generation, Baby Boomers, Generation X, Generation Y, Generation Z), as well as for the different age groups of each generation (<18, 18-25, 26-64, 65+). In parallel, the corresponding population sizes and the years of the different types of crashes were determined so as to guarantee a reliable and comparative evaluation of the generations. It emerges from the application of Log-Linear regression models that the number of road casualties follows a rising trend in the transition from the older to the younger generations, which presumably can be attributed to increased mobility of younger generations. Additionally, most car crash victims between the ages of 26 and 64 belong to Generation X while those involved in a two-wheeled vehicle accident belong to Generation Y.  This is most probably due to the fact that the members of the two generations are connected to different financial periods but also to the tendency of the members of Generation Y to experience delays in their transition to the following stages of their life, which normally involves the acquisition of a private car, thus rendering the choice of a motorbike for their transportation inevitable.