To address the large deformation and instability of gob-side entry roofs in soft, thick coal seams induced by residual cavities left by hydraulic flushing, the 1609 working face of Jiulishan Coal Mine was selected as the engineering background. Field investigation, numerical simulation, and industrial field testing were combined to investigate the deformation and failure characteristics of surrounding rock and the corresponding control technology for gob-side entries with cavity-bearing roofs. The results indicate that residual cavities created by hydraulic flushing disrupt the stress transfer path within the roof, causing stress field distortion and expansion of tensile stress zones, thereby significantly weakening the roof load-bearing capacity. As the cavity size increases, the surrounding rock deformation and plastic zone continuously expand. When the cavity size exceeds 1.0 m, roof subsidence exhibits a nonlinear increase, and the fractured zone around the cavity connects with the roof plastic zone, forming a continuous failure band that serves as the key factor leading to surrounding rock instability. Based on the deformation characteristics of the cavity-bearing roof, namely shallow fragmentation, deep-seated separation, and structural instability, a collaborative control technology consisting of multi-level cable bolts, steel-beam reinforcement, and grouting through injection pipes was proposed. By establishing a shallow–intermediate–deep hierarchical load-bearing structure and reinforcing the fractured cavity zone through grouting, the technology reconstructs the surrounding rock load-bearing system and optimizes the stress environment. Field application results show that, for a roof containing a 1.5 m cavity, the maximum roof subsidence and separation were controlled within 102 mm and 55 mm, respectively, and the roadway maintained a stable condition throughout the monitoring period. The findings provide both a theoretical basis and engineering guidance for surrounding rock control of gob-side entries with cavity-bearing roofs in soft, thick coal seams.