In this study, the transfer and dissipation of strain energy in the surrounding rock of a deep roadway were analyzed, considering the objective strain softening and dilatancy behaviors. The strain energy increment was decomposed, and its variation was analyzed based on the incremental plastic flow theory; then, a numerical simulation was conducted for verification and further analysis. The results were verified by the field monitoring data of a coal mine gateway. The results show that in the elastic stage, the volumetric elastic strain energy density Uev decreases, while the shear elastic strain energy density Ues increases. In the plastic stage, both Uev and Ues decrease. The volumetric plastic strain energy density Upv is negative, and its absolute value increases, leading to strain energy accumulation. In contrast, the shear plastic strain energy density Ups is positive and increases, leading to strain energy dissipation. Considering strain softening, the elastic strain energy decreases, the plastic strain energy increases, and the region of strain energy dissipation expands. Considering dilatancy, the plastic strain energy varies more significantly, and the effect of strain softening is amplified. The strain energy is transferred from the deep part to the shallow part of the elastic zone and then to the plastic zone. The preexisting and input strain energies in the plastic zone are transformed into considerable amounts of plastic strain energy and then dissipated. Thereafter, a significant plastic strain appears, leading to the large deformation of the surrounding rock.