To address the challenges in the collaborative control of strong mine pressure and surface damage during fully mechanized shallow soft coal seam top-coal caving mining, this study takes the 22,031 working face of Xindeng (Zhengzhou, China) Coal Mine as the research background. By combining analytical modeling and discrete-element granular flow simulation, this research elucidates how overburden fractures evolve and how the ground surface responds throughout the mining of shallow, soft coal seams. This research shows that the mechanical model analysis based on plate theory indicates that the first fracture of the immediate roof occurs 0.5 m from the goaf side of the mined-out area. Numerical simulations demonstrate that when the working face advances 80 m, the mining-induced influence extends to the surface. The displacement field of the overburden undergoes a dynamic temporal evolution law following the sequence of “rectangle–trapezoid” → “hyperbola-like” → “trapezoid”. During the advancement of the working face, the fracture pattern of the overburden evolves from “rectangle–trapezoid” to “trapezoid”, and the affected range on the surface transforms from an “inverted trapezoid” to a “trapezoid”. This study ultimately clarifies the dynamic law of collaborative deformation between the overburden and the surface, providing a theoretical basis for the safe mining of shallow coal seams, the prevention of roof accidents, and the optimization of mining technology.