The important technical process to ensure the success of gob-side entry retaining by roof cutting (GERRC) was the advanced pre-splitting blasting to cut off the mechanical connection between the roadway and working face roof. The whole-cycle roof structure evolution and stress characteristics of GERRC were analyzed. The factors affecting the roof deformation of GERRC were analyzed, and the quantitative relationship between the roof deformation of GERRC and the support stiffness was determined. The results showed that the temporary support stiffness was higher, the support position to the side of the roof cutting was closer, and the roof subsidence deformation of GERRC was smaller. It is proposed to use a single support mass with a high stiffness to control the deformation of the roof, but it also made the support mass and roof elastic potential energy aggregate. To fully utilize the matching of the support stiffness and roof subsidence, improve the stability, and control the subsidence deformation of the roof in GERRC, double-row stacking supports were adopted in the inclination of GERRC, which were used to increase the stiffness of the support system.