A large coal pillar (usually more than 90 m) is generally left in place to ensure the stability of main roadway groups, due to its long service lifespan, which commonly also causes a significant loss of coal resources. The design of the width of the protective coal pillar and the control system of the surrounding rock are directly determined by the characteristics of the stress field and the damage mechanism under the influence of the mining activities. However, there are few studies on the effects of the partial-stress boosting and the direction deflection of the stress field on the failure evolution of the surrounding rock (especially in multi-seam mining). In this paper, theoretical analysis and numerical simulation are used to investigate the direction evolution of the maximum principal stress in front of the working face with malposition distances between the upper and lower working faces during the influence of double coal seams mining. Furthermore, a large-scale numerical model is used to study the deviatoric stress evolution of the surrounding rock and the propagation process of the plastic zone in the main roadway group with different widths of protective coal pillars. Then, an asymmetric cooperative anchoring classification method is proposed to strengthen the roadway support, depending on the critical area of the deviatoric stress in the roadway surrounding rock. The peak zone deflection of the deviatoric stress determines the evolution direction of the plastic area, and the peak value of the deviatoric stress presents a typical asymmetric stress boosting on both sides of the roadway. These findings are validated by the on-site ground pressure monitoring results and the practical failure modes of the surrounding rock.