With the increasing complexity of economic systems caused by the intensification of European integration processes and general globalisation trend, the problems of ensuring the optimal operation of transport companies are becoming especially important. Given these facts, the article's purpose is to develop and test a structural modelling algorithm based on the system state indicator (entropy of the structure of the export freight system). Research methods used in the article include: statistical (structure and dynamics analysis), systematisation and comparison, system analysis methods (entropy characteristics), mathematical programming methods. The mathematical formulation of problems involves studying structural uncertainty due to the synergistic influence of interconnected structures. As a result of the optimisation calculations, the entropy index decreased as a consequence of the optimisation of the studied structures of export cargo. The study results using structural-dynamic modelling provide an opportunity to determine benchmarks for optimising the structure of export transportation. Therefore, they can act as indicators in the relevant field to substantiate the performance of large transport and logistics companies. The use of such approaches will help improve cooperation on a shared basis between Ukraine and the countries of Central Europe. Implications for Central European audience: first of all, the algorithm of structural modelling containing stages is offered (structural-dynamic analysis; systematisation of the reasons that led to structural changes; mathematical formulation of the optimisation problem; numerical solution of the problem; interpretation of results and development of recommendations) as the theoretical contribution. Moreover, it has prospects for