Generation, propagation, and coalescence of the shear and tensile cracks in the gob-side filling wall are significantly affected by the location of the fracture of the critical rock block. The Universal Discrete Element Code software was used to investigate crack evolution characteristics in a gob-side filling wall and the parameter calibration process for various strata and the filling wall was clearly illustrated. The cracks in both the filling wall and the coal wall propagate inward in a V-shape pattern with dominant shear cracks generated initially. As the distance between the fracture and the filling wall decreases, the number of cracks in the filling wall decreases, and the stability of the filling wall gradually improves; thus, by splitting the roof rock at the optimal location, the filling wall can be maintained in a stable state. Additionally, we conducted a sensitivity analysis that demonstrated that the higher the coal seam strength, the fewer cracks occur in both the filling wall and the coal wall, and the less failure they experience. With the main roof fracturing into a cantilever structure, the higher the immediate roof strength, the fewer cracks are in the filling wall. With the critical rock block fracturing above the roadway, an optimal strength of the immediate roof can be found that will stabilize the filling wall. This study presents a theoretical investigation into stabilization of the filling wall, demonstrating the significance of pre-splitting the roof rock at a desirable location.