The abandoned mines causing settlement of the surface above and collapse of the cavities are the major influencing factor on the stability of the nearby underground structures. To prevent the harmful effect, the backfill methods are commonly applied to the cavities although the design criteria and the analysis method are not properly addressed in some cases. An approximate analytical method together with the numerical technique is considered in this study to simulate the gradual deterioration of the rock masses around the cavities and, therefore, the influential zone to the underground structures passing through the cavities. Also considered in this study is the backfill effect on the stability of the rock masses around the cavities. Specifically, the incomplete backfill effect is compared with that of the idealized backfill method by adopting elasto-plastic analysis involving a strain softening material law.