Taking the XV1311 working face of Chengzhuang Mine as the engineering background, a systematic study on the roof cutting and pressure relief parameters of the gob-side entry retaining in the XV1311 working face was conducted by combining theoretical analysis, numerical simulation, and field tests. First, the theoretical analysis determined the roof cutting height of 14.8 m, roof cutting angle of 20°, and roof cutting hole spacing of 2 m. Secondly, FLAC3D simulation was used to comparatively analyze the stress, displacement, and plastic zone distribution of the roadway surrounding rock under roof cutting and non-roof cutting conditions. The results showed that, compared with non-roof cutting, the vertical stress peak and stress concentration area of the roadway surrounding rock decreased under roof cutting conditions, while the range of the stress relief zone increased. Moreover, the goaf roof caving could completely fill the goaf, which helped to improve roadway stability. Field monitoring results indicated that the deformation of the roadway surrounding rock was effectively controlled, verifying the rationality of the roof cutting parameters.