Recently, governments of developed countries, such as Japan and other European and North America countries, have encouraged using forest resources to reduce carbon dioxide (CO2) emissions. Cross-laminated timber (CLT) is a solid wood panel commonly used as a structural material to construct moderate-to-large-sized buildings because of its high strength and stiffness. Hence, we proposed replacing reinforced concrete slabs with CLT floor panels in moderate-to-large-sized buildings. The push-out shear test was conducted to investigate the shear performance of the proposed connection method between steel beams and CLT panels. The experimental variables denote the fiber direction of a CLT panel concerning test loading and lubricant oil used for fastening hexagon head bolts. A testing machine was used to apply shear load in a vertical direction using a pressure plate and rotational pins. Based on the results, the lubricated specimens exhibited greater initial stiffness than the unlubricated specimens. In addition, lubricant oil facilitated the practical application of tensile forces to hexagon head bolts. European Yield Theory was used to evaluate the yield shear strength of each connection method.