Continuous mining of metal deposits leads the overlying strata to move, deform, and collapse, which is particularly obvious when open-pit mining and underground mining are adjacent. Once the mining depth of the adjacent open-pit lags severely behind the underground, the ultimate underground mining depth needs to be studied before the surface deformation extends to the open-pit mining area. The numerical simulation and the mechanical model are applied to research the ultimate underground mining depth of the southeast mining area in the Gongchangling Iron mine. In the numerical simulation, the effect of granular rock is considered and the granular rock in the collapse pit is simplified as the degraded rock mass. The ultimate underground mining depth can be obtained by the values of the indicators of surface movement and deformation. In the mechanical model, the modified mechanical model for the progressive hanging wall caving is established based on Hoke’s conclusion, which considers the lateral pressure of the granular rock. Using the limiting equilibrium analysis, the relationship of the ultimate underground mining depth and the range of surface caving can be derived. The results show that the ultimate underground mining depth obtained by the numerical simulation is greater than the theoretical calculation of the modified mechanical model. The reason for this difference may be related to the assumption of the granular rock in the numerical simulation, which increases the resistance of granular rock to the deformation of rock mass. Therefore, the ultimate underground mining depth obtained by the theoretical calculation is suggested. Meanwhile, the surface displacement monitoring is implemented to verify the reasonability of the ultimate underground mining depth. Monitoring results show that the indicators of surface deformation are below the critical value of dangerous movement when the underground is mined to the ultimate mining depth. The practice proves that the determination of the ultimate underground mining depth in this work can ensure the safety of the open-pit and underground synergetic mining.