Abstract: Road traffic crashes (RTCs) are a major problem for authorities and governments worldwide. They incur losses of property, human lives, and productivity. The involvement of teenage drivers and road users is alarmingly prevalent in RTCs since traffic injuries unduly impact the working-age group (15–44 years). Therefore, research on young people’s engagement in RTCs is vital due to its relevance and widespread frequency. Thus, this study focused on evaluating the factors that influence the frequency and severity of RTCs involving adolescent road users aged 15 to 44 in fatal and significant injury RTCs in Al-Ahsa, Saudi Arabia. In this study, firstly, descriptive analyses were performed to justify the target age group analysis. Then, prediction models employing logistic regression and CART were created to study the RTC characteristics impacting the target age group participation in RTCs. The most commonly observed types of crashes are vehicle collisions, followed by multiple-vehicle and pedestrian crashes. Despite its low frequency, the study area has a high severity index for RTCs, where 73% of severe RTCs include individuals aged 15 to 44. Crash events with a large number of injured victims and fatalities are more likely to involve people in the target age range, according to logistic regression and CART models. The CART model also suggests that vehicle overturn RTCs involving victims in the target age range are more likely to occur as a result of driver distraction, speeding, not giving way, or rapid turning. As compared with the logistic regression model, the CART model was more convenient and accurate for understanding the trends and predicting the involvement probability of the target age group in RTCs; however, this model requires a higher processing time for its development.