Considering the factors affecting the surrounding rock stability of gob-side entry retaining, the applicability of a large-diameter, concrete-filled steel tube roadside support body in a top-coal caving fully mechanized face is discussed, and a new approach to gob-side entry retaining is proposed in this study. The mechanical model of the surrounding rock structure of gob-side entry retaining in a top-coal caving fully mechanized face was established, the critical state of column–roof contact shear slip instability was clarified through Prandtl foundation failure theory, and the deformation mechanism of the surrounding rock of the retained roadway was analyzed through numerical simulation. The results indicated that the range of the tensile stress zone and extreme tensile stress of the roof between columns are closely related to the spacing of columns, which is the key factor influencing the deformation of the retained roadway. In addition, besides uncontrollable factors, the stability of the contact interface between the roof and columns is directly related to the area of the contact interface between the concrete-filled steel tubes and the roof, and the size of the critical contact area is directly related to the properties of top-coal mass. Finally, a field test was carried out in 91–101 working panels in the Wang-Zhuang Coal Mine; the maximum convergence of the roof and floor was 510 mm, and the area of the retained roadway section reached 12.9 m2, which is within a reasonable range.