Due to the viscoelasticity of rubber materials, hysteresis loss due to deformation is the main reason for the rolling resistance of high-speed rubber tracks. Since the structure and material of high-speed rubber track assemblies are different from traditional tires and metal tracks, the rolling resistance theory of traditional wheeled and tracked vehicles is not applicable. Therefore, in order to determine the rolling resistance scientifically and accurately, the mechanism research of the rolling resistance of high-speed rubber track assembly is the key to the design of high-speed rubber crawler vehicles. In this paper, the stress–strain characteristics of rubber track under the action of compression, tension, bending, and driving were studied. The strain load spectrum of rubber tracks was established, and the strain cyclic load was extracted by the rainflow method. The temperature model of the rubber track was developed based on its dynamic characteristics. On the basis of energy conservation, the hysteresis loss of rubber is equivalent to the energy consumption of rolling resistance, and the theoretical model of rolling resistance of high-speed rubber track assembly is established. In accordance with the model above, the key influencing factors and changing trends of rolling resistance are analyzed, which provides a theoretical basis for the performance optimization of high-speed rubber track assembly.