A high-carbon, high-silicon steel (1.21 wt% C, 2.56 wt% Mn, 1.59 wt% Si) was subjected to quenching from 900 and 1000 °C, resulting in microstructures containing 60 and 94% of retained austenite, respectively. Subsequent abrasive wear tests of quenched samples were performed using two-body abrasion and three-body abrasion testing machines. Investigations on worn surface and subsurface were carried out using SEM, XRD, and microhardness measurement. It was found that the highest microhardness of worn surface (about 1400 HV0.05) was achieved on samples quenched from 900 °C after three-body abrasion. Microhardness of samples after two-body abrasion was noticeably smaller. with a maximum of about 1200 HV0.05. This difference correlates with microstructure investigations along with XRD results. Three-body abrasion has produced a significantly deeper deformed layer; corresponding diffractograms show bigger values of the full width at half maximum parameter (FWHM) for both α and γ alone standing peaks. The obtained results are discussed in the light of possible differences in abrasive wear conditions and differing stability of retained austenite after quenching from different temperatures. It is shown that a structure of metastable austenite may be used as a detector for wear conditions, as the sensitivity of such austenite to phase transformation strongly depends on wear conditions, and even small changes in the latter lead to significant differences in the properties of the worn surface.