Bending stiffness (BS) is one of the two most important mechanical parameters of corrugated board. The second is edge crush resistance (ECT). Both are used in many analytical formulas to assess the load capacity of corrugated cardboard packaging. Therefore, the correct determination of bending stiffness is crucial in the design of corrugated board structures. This paper focuses on the analytical determination of BS based on the known parameters of the constituent papers and the geometry of the corrugated layers. The work analyzes in detail the dependence of the bending stiffness of an asymmetric, five-layer corrugated cardboard on the sample arrangement. A specimen bent so that the layers on the lower wave side are compressed has approximately 10% higher stiffness value. This is due to imperfections, which are particularly important in the case of compression of very thin liners. The study showed that imperfection at the level of a few microns causes noticeable drops in bending stiffness. The method has also been validated by means of experimental data from the literature and simple numerical finite element model (FEM). The obtained compliance of the computational model with the experimental model is very satisfactory. The work also included a critical discussion of the already published data and observations of other scientists in the field.