Purpose. The paper aims to propose an approach to shape the sustainable strategies of freight forwarders under uncertainty of the stochastic environment of the transportation market. Methodology. The elements of the game theory were used to formalize the conflict situation, where the uncertainty of the transport market is considered as a game with nature. To design the model of the freight transportation market, the principles of the system’s theory were used in the representation of a forwarding company operating as an element within the macro-logistic system of the transport market. The methods of object-oriented programming were applied to develop the dedicated software for computer simulations of the forwarder’s operation within the market of transport services. The regression analysis was used as the main methodology to process the numeric results of experimental studies. The elements of functional analysis were applied to substantiate the sustainable strategy of a forwarding company in the considered example. Findings. The results of the conducted experiment allowed for determining the high-quality dependencies between the number of serviced requests and the number of dispatchers involved in the requests’ servicing for the case when the operators’ decisions are supported by the specialized software and for the case when decisions are made conventionally. Originality. The use of a game-theoretical approach in this study is based on the advanced simulations of a freight servicing process where the demand randomness and the servicing process stochasticity are integrally considered. Practical value. The proposed methodological approach is proposed to be used by forwarding companies to evaluate sustainable strategies when servicing clients within the given market. The use of the developed approach in practice allows forwarders to decrease the operational costs achieving the minimal negative impact on the environment.