Based on the application of the retained gob-side entry in a fully mechanized face E2307 headgate, the stress distribution and deformation characteristics of the roadside backfill body for different types of roof cutting were investigated in this study by employing a combination method of theoretical analysis, numerical simulation, and field measurement. The study uses RocLab software to accurately modify the lithology of the simulation area, discuss the position of roof cutting and the pressure relief parameters of roof cutting, and select the optimal solution of the roof-cutting plan. The results show that the advanced pre-cracking effectively blocks the stress transmission in the high-level roof strata; the roadway is in the stress unloading zone, the stress environment of the surrounding rock in the roadway is significantly optimized, and the deformation of the surrounding rock in the roadway is significantly reduced. In the roof-cutting scheme, the deformation of the surrounding rock in the 90° main roof-cutting scheme is reduced by 78% compared with the uncut roof and by 39% compared with the 90° immediate roof cutting. The research results were successfully applied at the E2307 headgate of the Gaohe coal mine; the maximum roof subsidence and the maximum rib convergence were 121 and 74 mm, respectively. Field monitoring indicates that the deformation of the retained entry was controllable, and the final retaining effects were good.