Underground coal mining leads to land subsidence, which, in turn, results in damage to buildings and infrastructure, disturbs the original ecological environment, and hinders the sustainable development of coal mining cities. A reasonable estimation of land subsidence, on the other hand, is the foundation for building protection, land reclamation, and ecological environment reconstruction. However, when we applied the existing land subsidence estimation theory to the deep mining areas of the Ordos coalfield in western China, there was a significant deviation between the estimations and the measurements. To explain such unusual case, we propose using the overburden’s average GSI (Geological Strength Index) value instead of the compressive strength (UCS) of rock specimens for a better representation of the overburden’s overall properties. By using on-site subsidence monitoring results and historical data, we provided evidence which supports that the overburden’s average GSI value has a much greater impact on subsidence rates than the UCS. Subsequently, we investigated the relationship between three typical overburden’s GSI values and the subsidence rates via a calibrated numerical model, revealing the variation patterns of maximum surface subsidence when the overburden’s average GSI value is set at 30, 50, and 75, respectively. Finally, on the basis of the measured and simulated results, we discussed a non-conventional strip mining method for mining subsidence control in the deep mining areas of the Ordos coalfield in western China, and explained why it is possible and what are the significant advantages behind. The proposed methods, findings, and suggestions in this paper are therefore quite helpful for researchers and engineers who wish to estimate and control the mining-induced land subsidence, as well as for those who are particularly interested in the study of environment science related to land subsidence.