One of the most important ways to reduce energy consumption in belt conveyor transportation along horizontal routes of significant length is to ensure limited belt indentation rolling resistance. This type of resistance results from the cyclical compression of the bottom cover of the belt by idlers as the belt moves over successive idler sets. This paper presents a method for testing the dynamic properties of rubber subjected to cyclical compression. The presented analysis is multiaspect. The method parameters have been optimized to match one of the theoretical models of indentation rolling resistance calculations. The tests of dynamic properties were performed for five different rubber types and included calculations of the belt damping factor and modulus of elasticity. The theoretical model allowed for the calculations of belt indentation rolling resistance. The results were verified in indentation rolling resistance tests performed on a test rig designed for steel-cord belts. The measurements were performed for belt specimens with covers made of the tested rubber types. The calculation results highly correlated with the measurement results. The proposed method for testing the dynamic properties of rubber can not only provide data required in the calculations of the power demand from belt conveyors but also serve conveyor belt manufacturers in their search for rubber compounds used in belts that generate lower indentation rolling resistances.