Understanding the shear behavior of the interface between surrounding rock and backfill is of significant engineering importance for enhancing stope stability in cemented tailings backfill mining. However, the evolutionary mechanisms of shear properties and damage under varying mechanical conditions remain insufficiently studied. This investigation employed tailings and surrounding rock from a Guangdong tailings pond, with basic mechanical parameters determined through laboratory tests. Numerical models of the rock-backfill composite were developed using PFC2D, considering different shear rates (0.3, 0.6, and 0.9 mm/min), lateral confinement levels (0.5, 1.0, and 1.5 MPa), and roughness coefficients. The analysis compared the interface’s peak and residual shear strengths, revealed crack evolution patterns, and explored damage mechanisms using acoustic emission monitoring and energy dissipation theory. Key findings include the following: (1) Shear stress–displacement curves under all conditions exhibited three stages, ascending, shearing-off, and sliding, with distinct peak and residual strengths. (2) Increasing lateral confinement, shear rate, and roughness transformed failure from localized to global sliding, with cracks occurring at the interface and propagating into the backfill. (3) Cumulative acoustic emission events increased with all three factors, with lateral confinement showing the most substantial effect on interface energy accumulation (83% increase). These results provide theoretical support for assessing interface stability in deep backfilled stopes.