Twelve blocks of Cross Laminated Timber (CLT) were built, tested and simulated. Three types of blocks with different laminate directions in the middle/second layers were used: 0/30/0, 0/45/0 and 0/90/0. Simulations with three-dimensional quadratic orthotropic linear elastic finite elements were conducted. The goal was to compare tested in-plane shear stiffnesses for CLT blocks made from Norway Spruce (Picea abies) boards of C24 quality with a finite element (FEM) simulated block stiffness. Three-layer CLT were studied with block dimensions of 600 x 600 x 45 mm. The first and last layer laminate directions were assumed to be 0○. The middle layer laminate directions were 30○, 45○ and 90○. A 1 mm gap was assumed between the side edges. The glued contact surfaces were assumed to be perfectly glued with rigid glue in the simulations. In the practically tested blocks a PVAc D2 classified glue was used. All blocks were simulated and tested in the same loading arrangement as the practical test set-up. The blocks were compressed in the diagonal direction. Blocks of 0/30/0 and 0/45/0 were compressed twice, once over each diagonal. The 0/90/0 blocks were compressed over one diagonal. A total of 19 practical compression tests was performed; in all cases, the displacements were measured in the force- and orthogonal direction. The stiffest loading case, measured in the force direction, was the loading arrangement 0/45/0-A. The weakest loading case, measured in the force direction, was the loading arrangement 0/30/0-B. The same result could be concluded from the FEM simulations. The calculated stiffness in the loading direction was between 1.21 – 1.87 times larger than the measured stiffness. The models pressed in the “weakest” direction gave the largest difference between the simulated and measured stiffness.