Glued-in perforated steel plate (GIPSP) connections demonstrate significant shear strength and high slip modulus. Consequently, they indicate substantial potential for application in timber–concrete composite (TCC) structures according to the emerging tendencies in high-storey and large-span buildings. However, the application pattern in prefabricated TCC structures and the theoretical analysis of the shear performances of GIPSP connections are highly deficient. This hinders the application of this type of shear connection. In this study, the shear performances of GIPSP connections were evaluated using push-out tests. Ten groups of push-out specimens with different steel plate numbers, steel plate lengths, and concrete slab types were tested. The concrete slab types investigated in the experiments included a prefabricated concrete slab and cast-in-situ concrete slab. The experimental results were discussed in terms of the failure mode, load-carrying capacity, and slip modulus. The theoretical models for the load-carrying capacity related to the associate failure mode were discussed based on an analysis of the failure mechanisms. In addition, design proposals with regard to the load-carrying capacity and slip modulus of the GIPSP connection were presented. The research results can provide design guidance for TCC beams using GIPSP connections and prefabricated concrete slabs.