To ensure the secondary reuse effect of small coal pillar-gob-side entry retaining, taking the bilateral gob-side entry retaining of 150207 transport crossheading of Yangchan Coal Industry as the engineering background, the theoretical analysis and numerical simulation methods are used to study the fracture characteristics of overburden rock structure after primary mining and secondary mining of roadway roof. The mechanical model of bilateral gob-side entry retaining roadway is established, and the core influencing factors of large deformation of surrounding rock of gob-side entry retaining are obtained. The roof cutting and pressure relief technology of bilateral gob-side entry retaining roadway is proposed, and the key parameters of roof cutting and pressure relief are determined. The field application results show that the technology can effectively suppress the convergence deformation of the surrounding rock of the retaining roadway and meet the return air demand of 150209 working face. The research in this paper has certain reference value for the gob-side entry retaining project under similar conditions.