Corrugated boards are used for packaging because of their high strength-to-weight ratio, recyclability, and biodegradability. They have an orthotropic sandwich structure with unique characteristics for each direction owing to their flute shape. In this study, the bending behavior was qualitatively analyzed for various variables through an FE-based simulation, and the possibility of an alternative test method for the four-point bending test on a corrugated board was examined through a similarity analysis with the experimental results. The cross-machine direction (CD) bending stiffness through finite element analysis (FEA) simulation was closely related to the thickness of the corrugated board. In AB-flute-double-wall (AB/F-DW), the difference in CD bending stiffness based on the bending direction was approximately 17.2% in the FEA simulation and approximately 10.5% in the experiment. However, the differences in the bending behavior (bending force vs. deflection plot) and bending stiffness based on the phase shift between the two flutes constituting BB-flute-double-wall (BB/F-DW) were insignificant. Overall, the CD bending behavior of the corrugated board was simulated relatively well through FEA simulation. However, it was impossible to simulate the machine-direction (MD) bending behavior through FE-based simulation because of a decrease in convergence and a large error caused by the variability of the contact condition of the modeled test specimen with a non-uniform MD cross-section.