A new method was developed to apply pull-and-shear loads to the bolt specimen in order to evaluate the anchorage performance of the rebar bolt and the D-Bolt. In the tests, five displacing angles (0°, 20°, 40°, 60°, and 90°), two joint gaps (0 mm and 30 mm), and three kinds of host rock materials (weak concrete, strong concrete, and concrete-granite) were considered, and stress–strain measurements were conducted. Results show that the ultimate loads of both the D-Bolt and the rebar bolt remained constant with any displacing angles. The ultimate displacement of the D-Bolt changed from 140 mm at the 0° displacing angle (pure pull) to approximately 70 mm at a displacing angle greater than 40°. The displacement capacity of the D-Bolt is approximately 3.5 times that of the rebar bolt under pure pull and 50% higher than that of the rebar bolt under pure shear. The compressive stress exists at 50 mm from the bolt head, and the maximum bending moment value rises with the increasing displacing angle. The rebar bolt mobilises greater applied load than the D-Bolt when subjected to the maximum bending. The yielding length (at 0°) of the D-Bolt is longer than that of the rebar bolt. The displacement capacity of the bolts increased with the joint gap. The bolt subjected to joint gap effect yields more quickly with greater bending moment and smaller applied load. The displacement capacities of the D-Bolt and the rebar bolt are greater in the weak host rock than that in the hard host rock. In pure shear condition, the ultimate load of the bolts slightly decreases in the hard rock. The yielding speed in the hard rock is higher than that in the weak rock.