This study investigates the wear micromechanisms of D2 steels under impact-sliding conditions, offering insights into their performance when used in applications such as trimming dies for high-strength steel sheets where they undergo plastic deformation and chipping. Two D2 steel samples, both with a bulk hardness of 59.7 HRC but different matrix hardnesses and carbide distributions, are tested by using an impact-sliding wear test rig at Hertzian contact pressures exceeding 2 GPa. The sample with a softer matrix exhibits wear primarily through delamination caused by plastic deformation. This initiates cracks at the matrix/primary carbide interface, leading to material loss in the form of large chips. In contrast, the steel with a harder matrix shows reduced wear due to its resistance to plastic deformation. Initially, wear occurs through the fracture of primary carbides. However, with prolonged loading, the matrix begins to soften, adopting a wear mechanism similar to the D2 steel with softer matrix. Notably, smaller primary carbides are associated with improved wear resistance by limiting the initiation sites for cracks, especially at the matrix/primary carbide interface. This understanding enables the selection and design of heat treatments to optimize D2 steel microstructure, thus improving resistance to impact-sliding wear damages observed in processes like trimming.