In this study, five full-scale bolted glulam beam-to-beam connections with slotted-in steel plates were conducted under a third-point loading, and a three-dimensional finite element method based model was also established to investigate the failure modes and moment resistance of such connections. A material model based on the Continuum Damage Mechanics (CDM) theory was developed to predict damage evolution of wood. Different damage variables were used to consider the ductile and brittle failure modes of wood, respectively. The test results indicated that splitting and shear plug failures were the main failure modes. The numerical analysis model prediction achieved fair agreements with the test results. The research could provide the guide for the design of bolted beam-to-column connections in heavy timber structures.