To address the challenges associated with surrounding rock control in gob-side entry retaining, No. N3-13 and N3-15 Faces in Changcun Coal Mine were taken as engineering backgrounds. Using the UDEC numerical simulation method, a comparative analysis was conducted on the deformation characteristics of the surrounding rock under three scenarios: no support, original support, and optimized support. Additionally, the influence of different roof-cutting heights (10 m, 14 m, and 21 m) on the caving behavior of the gob roof and the stress distribution in the surrounding rock was systematically investigated. The results indicated that the optimized support scheme, by incorporating an inclined tensioned anchor cable structure, effectively limited roof displacement to within 420 mm and reduced the rib displacement to 50 mm, representing reductions of approximately 57.14% and 90.70%, respectively, compared to the original support. When the roof-cutting height reached 21 m, the vertical stress in the roof decreased by about 21%, significantly improving the stress environment and enhancing the overall stability of the entry.