A stability analysis of a laterally confined slope model, lying on an inclined bedding plane, was presented to evaluate the lateral shear resistance by considering the loading paths and failure envelopes. Two slope models were prepared on a bedding plane by compaction, one with and one without lateral confinement. The compacted models are related to the geological conditions at shallow depths where brittle deformation can occur and an excavation can induce horizontal field stress that significantly influences the stability of the slope. Three distinct loading paths, controlled by either tilting the angles or increasing the surcharge loads, were applied to achieve the failure of the slope models. Rankine’s passive earth pressure due to compaction was reduced by the shear strength reduction ratio. The shear strength reduction ratio was estimated through the least-squares fitting method based on the results of model tests at failure when the loading paths intersected the failure envelope. Provided that the effect of lateral confinement in a rock mass can be described by the shear strength reduction ratio, the proposed equations will be beneficial for slope stability analyses of laterally confined slopes on bedding planes. A case study of an undercut pit wall in an open-pit mine was demonstrated by showing that the unknown shear strength reduction ratio can be back-analyzed from the rainfall-induced landslide case. Therefore, the design of other undercut slopes with different geometries and groundwater conditions in the rock mass, which have undergone the same geological process as the back-analyzed case, is possible.