This work aimed to perform the numerical and experimental analysis of three test setups (bending, vertical shear, and inclined shear) of CLT used to determine the rolling shear stiffness and strength. CLT specimens were manufactured with four different Brazilian wood species and two-component polyurethane adhesive. The stress distributions in the CLT test setups were simulated by Finite Element Method using ANSYS software. Rolling shear stiffness and strength was directly proportional to wood density. The CLT stiffness differed for each test setup. CLT strength was independent of the applied test setup. The numerical models provided the stress distribution in the areas of most interest of the specimen models which justified the failure modes obtained in the experimental tests. The inclined shear specimen was the one that best represented failure by rolling shear.