The anisotropic material behavior of wood, considered as a cylindrically orthotropic material with annual rings, leads to several diferent failure mechanisms already under uniaxial stresses. Stress interaction becomes important in the engineering design of structural elements and is often predicted by failure criteria based on uniaxial properties. The prediction quality of failure criteria has been assessed with longitudinal shear stress interaction, though less is known on rolling shear stress in interaction with stress perpendicular to the grain. The study aims at investigating the corresponding mechanical behavior of Norway spruce (Picea abies) clear wood by validating failure envelopes for stress combinations in the cross-sectional plane, based on experimental investigations. For this purpose, a test setup that controls the stress interaction and loading of clear wood along pre-defned displacement paths needed to be developed. Experimentally defned failure states could then be compared to failure surfaces predicted by the phenomenological failure criteria. Material behavior was quantifed in terms of stifness, strength, and elastic and post-elastic responses on dog-bone shaped specimens loaded along 12 diferent displacement paths. A comparison with failure criteria for two nominal compressive strain levels showed that a combination of failure criteria would be required to represent the material behavior and consider the positive efect of compressive stresses on the rolling shear strength. The fndings of this work will contribute to studying local stress distribution of structural elements and construction details, where stress interactions with rolling shear develop.