The i-DREAMS project has a core objective: to establish a comprehensive framework that defines, develops, and validates a context-aware 'Safety Tolerance Zone' (STZ). This zone is crucial for maintaining drivers within safe operational boundaries. The primary focus of this research is to conduct a detailed comparison between two machine learning approaches: long short-term memory networks and shallow neural networks. The goal is to evaluate the safety levels of participants as they engage in natural driving experiences within the i-DREAMS on-road field trials. To accomplish this objective, the study gathered a series of trips from a sample group consisting of 30 German drivers, 43 Belgian drivers, and 26 drivers from the United Kingdom. These trips were then input into the aforementioned machine learning methods to reveal the factors contributing to unsafe driving behaviour across various experiment stages. The results obtained highlight the significant positive impact of i-DREAMS' real-time interventions and post-trip assessments on enhancing driving behaviour. Furthermore, it is worth noting that neural networks demonstrated superior performance compared to other algorithms considered within this research context. ; The research was funded by the EU H2020 i-DREAMS project (Project Number: 814761) funded by the European Commission under the MG-2-1-2018 Research and Innovation Action (RIA).