Rail grinding and wheel turning can effectively remove surface defects and unevenness, which is a crucial process for the safe and smooth operation of trains. Machined surface integrity of wheel/rail materials significantly influences their tribological property. In this study, firstly, the rail blocks were ground via a cylindrical grinding machine, and the wheel rings were turned by a computer numerical control (CNC) lathe with varied parameters. Then, the sliding wear and damage characteristics of the machined wheel/rail samples under dry conditions were studied by virtue of a block-on-ring tribometer. The results show that the surface microhardness of the ground rail blocks is larger than that of wheel rings, while the surface roughness and the thickness of the subsurface plastic deformation layer (SPDL) of rail blocks are much smaller than those of wheel rings. After sliding, the surface microhardness of wheel/rail samples increases remarkably. The thickness of the SPDL, the wear loss, and the increase degree of surface microhardness of rail blocks are larger than those of wheel rings. Surface microhardness, roughness and the SPDL of the machined wheel/rail samples impose a combined influence on the anti-wear property, and the tribological pair with proper initial surface roughness and microhardness engenders the smallest amount of total wear loss.