EN 1.4301 (austenitic), EN 1.4509 (ferritic), EN 1.4162 (duplex) and EN 1.4310 C1000 (metastable austenitic) stainless steels were tested in lubricated sliding against an ingot cast EN X153WCrMoV12 and powder metallurgy nitrogen alloyed Uddeholm Vancron 40 tool steels to reveal critical to galling contact pressure, Pcr. The calculated Pcr were higher for steels with higher strength. At P>Pcr, due to plastic flow of sheet material, the tool is damaged substantially and wear-induced matrix damage causes rapid galling initiation. At P<Pcr, galling was not observed. The powder metallurgy tool steel was more resistant to galling against all tested stainless steels. Better performance was associated with fine and homogeneously distributed hard phases preventing intensive wear of the tool steel matrix.