Cross-toothed flange connections are used in drivetrains for form-fit coupling of shafts. They belong to the group of non-shiftable couplings. Compared to frictional connections, tooth flange connections can transmit significantly higher torques in the same space. In contrast to other tooth couplings, the crossed tooth flange coupling investigated here is characterized by a particularly complex load distribution. The preload force, which is necessary to transmit operational loads, is generated by tensioning bolts, which can be located centrally or decentralized. Thus, the stress condition in the notch of the coupling is always determined by a superposition of stresses from preload force and operating loads.Extensive experimental and simulative investigations were carried out as a part of a research project. In addition to the development of a pragmatic, specially adapted calculation concept for cross-toothed couplings for practice, the experimental tests were accompanied by calculations with the FKM guideline “Analytical Strength Assessment” and the FKM guideline “non-linear”, The determination of local stresses was carried out with the help of elasticity theoretical and elastic-plastic FE full-contact calculations based on experimentally determined material data.This article deals with the possibilities of calculations based on the FE simulation results using the above mentioned FKM guidelines. The experimentally determined load-carrying capacity is critically compared to the calculation results. The focus is on the implementation of the fatigue strength analysis in the context of the corresponding boundary conditions. Topics such as the assumed knee point of the Wöhler curve to the fatigue strength range are discussed as well as the evaluation options for elastic-plastic FE results for the guideline „non-linear”.