This article deals with the modernization of an existing loading system for the analysis of elastic–plastic properties of sheet metals in plane stress. The identification of the beginning of plastic deformation of sheet metal in plane strain is important in the cold pressing of sheet metal and in the assessment of the load capacity of thin-walled structures in the automotive and aerospace industry. The design of the control structure of the hydraulic part of the loading system for cross testing was carried out to automatize the whole process of experimental evaluation. For this purpose, proportional pressure-reducing valves together with control electronics were designed. Thus, the loading system is a control system for which a control algorithm has been designed and implemented on a PC. A computer simulation was performed to verify the functionality of the load system. An FEM simulation was performed to verify the correctness of the proposed numerical models and to confirm the experimental results. A numerical nonlinear model of the selected material was applied for the specification of plastic deformations. From the results, it is possible to state the appropriateness of the used models as well as the appropriateness of using modernized equipment for subsequent analysis of the plastic deformation of cruciform specimens.