This study explores the rolling shear properties of cross-laminated bamboo (CLB), an innovative engineering bamboo material. Two typical test methods are used for the experimental work: the modified planar shear tests (MPS) and the three-point short beam bending tests (SBB). The rolling shear strength and modulus are measured in MPS. The shear analogy method is used to calculate the rolling shear strength in SBB. Subsequently, comprehensive numerical models of MPS and SBB are developed, taking into account the material properties of bamboo and adhesives through user material and cohesive zone model. The stress-strain curves and failure propagations of the models align very well with the experimental results. Rolling shear failure was initiated at the interface between the middle layer and outside layer and extended diagonally. Parametric analysis on the cohesive strength of the MPS model shows the variation of loading curves and failure modes. The failure modes of SBB under different span-to-depth ratios are investigated by integrating the shear analogy method and numerical model.