Cross-laminated timber (CLT) is an innovative wood product that can be used to build midrise and tall wood construction as an alternative to concrete, masonry, and steel. As floor, roof, and wall made of CLT is subjected to out-of-plane bending, rolling shear (RS) failure of cross-layers can arise prior to bending failure of the outermost layers, which governs the load-carrying capacity of CLT. In fact, the global deflections of CLT depend on the rolling shear modulus of cross-layers, which is much lower than shear modulus parallel to grain. Therefore, it is necessary to determine and improve the rolling shear strength and modulus of cross-layers. In this paper, several test methods were firstly summarized, after which the main influence factors on rolling shear properties were reviewed. Finally, seven configurations of hybrid CLT with three layers were tested to assess the rolling shear properties of hybrid CLT, in which the outer layers are made of Spruce-Pine-Fir (SPF) and the cross-layer is made of different materials such as birch, compressed wood (CW), laminated veneer lumber (LVL), Parallel strand lumber (PSL), plywood, oriented strand board (OSB), and glued laminated bamboo (GLB). The CLT made of SPF was also tested, whose rolling shear properties were regarded as reference. The rolling shear properties of GLB are about twice as high as those of SPF. Other materials do not exhibit superior rolling shear properties to SPF. The compressed wood shows a significant ductility in rolling shear failure.