Gob-side entry driving near an advancing working face can improve the recovery rate of coal resources and keep the balance between mining and development. However, the large displacement of the gob-side entry caused by the mining dynamics of abutment pressure challenges the safety and processes of coal mining. This article takes the 15102 tailentry of Xizhang Coal Mine in Changzhi City, Shanxi Province, as an example to study the stability of the coal pillar and the failure characteristics of the surrounding rock and proposes cooperative control strategies of surrounding rock stability. Field tests indicated that when the coal pillar width was 15 m, the displacements of the entry floor, roof, coal pillar side, and solid coal side were 1121 mm, 601 mm, 783 mm, and 237 mm, respectively. A meticulously validated numerical model, incorporating a double-yield model for the gob materials and calibrated parameters, was developed to investigate the stress changes and yield zone distribution across the coal pillar with different sizes. The results of the simulation indicate that the influence range of the dynamic abutment pressure caused by mining in the upper section of gob-side entry driving is 30 m ahead and 70 m behind. When the coal pillar width increases from 7 m to 20 m, the internal stress of the coal pillar increases continuously, while the internal stress of the solid coal decreases continuously. It is estimated that the reasonable coal pillar width should be 7 m, which is subjected to a lower load. The cooperative control strategies comprising a narrow coal pillar, hydraulic fracturing roof cutting for pressure relief, and entry dynamic support were proposed and applied in the 15103 tailentry. The final displacements of the floor, roof, coal pillar side, and solid coal side were 66.01%, 62.06%, 61.05%, and 63.30% lower than that of the 15102 tailentry in the same period, respectively, which effectively controlled the stability of surrounding rock. In addition, this finding for the gob-side entry driving near an advancing working face in this study can potentially be applied to other similar projects.