Self-tapping screws, thanks to the speed and ease of installation have become more and more popular in the last 25 years. Slip modulus and strength increase when the screw axis is inclined with respect to the normal to the sliding plane, however, in this configuration screw is subjected to axial and shear force, together with bending moment. Moreover, interlayers having poor mechanical properties are often inserted between main connected members to ensure human comfort in the buildings or because it is required by the structural system. The complex interaction between axial and transversal behaviour of inclined screws may not be fully considered by some of the simplifed models in literature and codes, in this paper the behaviour of steel-to-timber connection is experimentally assessed and a finite element model of non-linear beam on foundation is validated. Experimental results are compared with the results of finite element analysis and with the Eurocode 5 model results.