The most important factor affecting the quality of transportation heavy goods is safety and security. Risk evaluation and management is one of the key issues during the planning oversized goods safe transportation and investments into transport infrastructure reconstruction. Usually it is international transportation and decision-making requires through analysis of the problem both, on the national and international scale and only then the most rational decision (transportation route) can be made with the view of the effective risk lowering, i.e. seeking the last possible reconstruction costs. The objective of the risk evaluation when investing into infrastructure reconstruction is to safeguard heavyweight or oversized goods transportation. When making the quantitative and economic assessment of the risk the theory of chances and mathematic statistics are most commonly used methods, because they are denoted to describe an event or process in case of ambiguous possibilities.