The spatial–temporal evolution law of shear damage on the joint surface is closely related to its morphological characteristics. Understanding the heterogeneous failure behavior of the joint surface is essential for revealing the controlling role of the joint morphology. The diorite from the Guanshan Tunnel is investigated through anisotropic direct shear tests in this study. Based on shear damage quantification and acoustic emission (AE) localization techniques, the heterogeneous damage evolution law of joint surfaces under different joint compression strength (JCS), normal stress (σn), and morphology parameter (M) is studied. The results indicate that the joint surface morphology, shear damage, and AE parameters exhibit similar anisotropic characteristics in different shear directions. An increase in the morphology parameter leads to an increase in shear failure, with shear fracture energy and the number of fracture events showing an increasing trend. Meanwhile, the occurrence of a large number of fracture points shifts from the pre-peak nonlinear period to the post-peak period. However, the evolution process of fracture events exhibits certain similarities, though the morphology parameters are different in two opposite shear directions. Additionally, shear damage volume and fracture energy demonstrate consistency in spatial distribution and quantitative characteristics, while the linear scale factor between cumulative shear fracture energy and damage volume decreases with increasing joint surface strength. These findings assist in a better understanding of the anti-sliding property of joint surfaces and provide crucial clues for further exploration of joint surface failure mechanisms.