The present research analyzes the safety and risk management principles and methods of oil and gas pipeline operation and examines how the hazard identification, risk assessment and successful contractor relationship can improve the process of safety management. This study is based on a comparative critical analysis associated with the effectiveness of specific safety and risk management practices, models and performance indicators that are applied by Oil and Gas multinational Companies so as to keep their pipeline operations reliable and safe. The sample of this research consists of two Oil and Gas pipeline owner Companies, the “Trans Adriatic Pipeline Company (TAP AG)” and the “Nord-Stream 2 AG” Company. These pipeline Companies will transport and provide natural gas throughout the Europe, enhancing the European energy security of supply with significant investments and advanced technological services in their pipeline construction and operational system. A comparative critical analysis between these two Companies in relation to the effectiveness of the safety and risk management system will be presented. The conclusions and research findings will answer the research questions, capturing the critical views of the researcher.