To evaluate the influence of different normal pressures and the fiber orientation on the in-plane compression behavior of paperboard during the deep drawing process, a new method was developed. In addition, the influence of the wrinkle formation on the dynamic coefficient of friction and the bending resistance was examined. To evaluate the eligibility of the in-plane compression testing method, a validation strategy was developed to compare the results from the new alternative tests with the punch force profiles from the deep drawing process within an empirical model.