This paper presents the design, implementation, and application of a dedicated experimental test rig developed to validate numerical models describing the interaction between vehicle running gear (wheel or track) or a demining roller and an anti-tank mine embedded in deformable soil. The proposed measurement system represents a realistic physical simulator of an anti-tank mine, reproducing the geometry and functional characteristics of real devices. It enables simultaneous measurements of the vertical displacement of the embedded object relative to the surrounding soil and the contact load applied by a wheel or a track system acting on the pressure plate of the mine’s fuse. The presented apparatus allows investigation of the influence of contact area on load transfer mechanisms and soil deformation response. This paper describes a series of tests conducted using the apparatus described under conditions representative of soil with reduced bearing capacity, where excessive settlement and load redistribution significantly affect the interaction process. Preliminary experimental results obtained for both wheeled and tracked running gears demonstrate distinct differences in the force–settlement response and loading characteristics between the two types of running gear, while also indicating that the developed apparatus and measurement methodology provide a consistent experimental basis for the future calibration of constitutive models and validation of advanced numerical approaches, including finite element, discrete element, or multibody dynamics methods.