High-temperature tribology, which is often involved during hot metal forming, is controlled via oxidation on a rubbing surface. However, for high chromium stainless steel (ST), where oxidation is strongly inhibited, the effect of counterface materials on tribological behavior is yet to be elucidated. In this study, the effects of counterfaces on the tribological behavior of 253MA ST and mild steel (MS) are investigated via a ball-on-disc test at 900 °C using a 20 N load. The results reveal that high-speed steel (HSS) experiences severe abrasive wear with MS and causes severe sticking problems with ST. Si3N4 and SiC present substantially stronger abrasive wear resistance than HSS with MS, and the friction coefficients are dependent on the type of ceramic. Both ceramics can facilitate the establishment of a thick tribo-oxide layer (> 3 µm) on ST to prevent sticking; however, this is accompanied by severe pull-out and fracture wear. The effects of the counterface on the mechanical properties of the tribo-oxide layer, near-surface transformation, and the responses of the tribo-oxide layer to friction and wear are discussed. This study contributes to the understanding of interfacial tribological behaviors when different types of tools are used on MS and ST.