Pile foundations frequently endure dynamic loads, necessitating an in‐depth examination of the cyclic shear properties at the pile–soil interface. This study involved a series of cyclic direct shear (CDS) tests conducted on sand and concrete with irregular surface, utilizing varying displacement amplitudes (1, 3, 6, and 10 mm) and joint roughness coefficients (0.4, 5.8, 9.5, 12.8, and 16.7). Discrete Element Method (DEM) models, informed by experimental data, facilitated mesoscopic mechanical response analyses. Findings indicate that the sand–concrete interface undergoes softening, with hysteresis loops' morphology dependent largely on displacement amplitude. A maximum ultimate shear stress corresponds to a specific critical surface roughness, while the initial tangent modulus escalates with increased concrete roughness. Volume variations of the specimen inversely correlate with displacement amplitude and directly with surface roughness. As displacement amplitude expands, there is a reduction in the maximum shear stiffness and an elevation in the maximum damping ratio. Empirical formulas for the surface roughness and normalized shear stiffness were proposed. Larger displacement amplitudes result in more substantial shear bands and heightened energy dissipation, yet the incremental energy ratio remains largely unaffected. Predominant energy dissipation mechanisms include both slip and rolling slip, with the former surpassing the latter in energy dissipation capacity. The anisotropy directions of contact normal, normal contact forces, and tangential contact forces consistently fluctuate with shear direction alterations.