One type of friction-type high-strength bolted connections (FHBCs) was developed to connect steel frames to the infilled cross-laminated timber (CLT) shear walls. In the FHBC, an opening was cut in the CLT near the wall-to-beam interface. Two predrilled holes existed within the CLT panel, running vertically from the bottom surface of the opening to the wall-to-beam interface. Two slotted holes were also predrilled on the top flange of the steel beam. Two high-strength bolts were attached to the upper anchor plate installed in the opening and the bottom anchor plate placed below the top flange of the steel beam. By applying the pretension force on the bolts, the CLT panel was pressed against the steel beam, forming the static friction force to resist the shear force along the wall-to-beam interface. In the study, cyclic tests were conducted to evaluate the friction properties of the interface between the infilled CLT wall and the steel beam. The CLT-steel friction coefficient was carefully investigated, which was a critical parameter for determining the maximum static friction force of the FHBCs. Three-dimensional solid finite element models were developed to predict the load-slip behaviors of the FHBCs, and their multi-stage load-slip behaviors were analyzed using the step-by-step method. It is found that the CLT-to-steel interface can perform with considerable shear-resisting capacity and shear stiffness in the pre-sliding friction as well as stable energy-dissipating capacity in its post-sliding behavior. The maximum static friction coefficient and the dynamic friction coefficient of the interface are recommended as 0.55 and 0.50, respectively. When the pretension force is enhanced from 40 kN to 80 kN, for the FHBCs with the three-layer CLT and those with the five-layer CLT, their ultimate shear-resisting capacity increases by 75.85% and 35.67%, respectively. The load-slip curves from the FHBC models exhibit a similar pre-sliding behavior with considerable shear stiffness and shear-resisting capacity. Whereas, the numerical load-slip curves of the post-sliding stage are distinctive between the FHBCs with the three-layer CLT and those with the five-layer CLT.