Nanostructured bainite (NB) bearing steel has excellent strength and ductility combinations, which can improve the fatigue life and wear resistance of bearing steel in harsh conditions. However, the phase transformations and the correlation between the microstructure and wear properties of NB bearing steel are still unclear. In this study, bearing steels with different Si contents (GCr15SiMo and GCr15Si1Mo) were prepared to have nano-bainitic structures, and their microstructure transformations and wear mechanisms were investigated. The results show that the Si element can inhibit the precipitation of carbides and can then promote the block-like retained austenite formation and refine the bainitic ferrite lamellar structure. The impact energy of GCr15Si1Mo is larger than that of GCr15SiMo because the nanostructured bainite and retained austenite are the main toughness phase in these steels. The wear results indicate that the steels which possess appropriate strength and toughness are helpful for improving wear resistance properties. Finally, the wear resistance performance of the GCr15Si1Mo austempered at 210 °C and GCr15SiMo austempered at 230 °C was good in this work.