High strength steels (HSS) used in highly abrasive environments, such as in mining and crushing, must endure high stress abrasion. To properly understand the wear behavior of materials under such circumstances, the connection between surface loading, work hardening, and material removal has first to be determined. In this study, wear resistant steels with initial hardness ranging from 400 to 750 HV were investigated in single-grit abrasion. In the cyclic abrasion experiments, the abrasion resistance of the steels was improved noticeably from the initial state due to surface hardening. However, the highest surface hardening rate did not result in the highest wear resistance. Moreover, when the surface loading was sufficiently increased, the transition to a high wear rate mechanism was observed.