Abstract: During hot stamping, the sliding contact between an aluminum alloy sheet and H13 tool steel often results in severe wear and adhesive material transfer. These tribological phenomena can significantly degrade forming quality and reduce die service life. In this study, the high-temperature tribological behavior of a heated 7075 aluminum alloy sheet sliding against H13 steel was investigated under conditions designed to simulate the aluminum hot-stamping practice. Experiments were conducted using a self-developed strip-type high-temperature friction tester. Based on the actual process sequence for aluminum hot stamping, the tester was used to reproduce a combined “solution treatment–forming–quenching” cycle such that the friction pair experienced thermal and mechanical histories similar to those encountered in industrial production. The main purpose was to elucidate how normal pressure and die surface condition influenced friction evolution, adhesive transfer, and the dominant wear mechanisms at elevated temperature. Three representative surface conditions of H13 steel were examined: (I) quenched and tempered (Q&T); (II) plasma nitrided after Q&T (PN); and (III) physical vapor deposition TiN coating applied after Q&T (PVD–TiN). Under different normal loads, the coefficient of friction and extent of adhesive wear/transfer were quantified and the friction and wear mechanisms were analyzed for each surface condition. The results show that as the normal pressure increases, the friction coefficient generally rises and adhesive wear becomes more severe. Higher contact pressure increases the real area of contact and promotes stronger interfacial bonding between the softened, high-temperature 7075 aluminum and steel surface, thereby accelerating sticking, tearing, and the formation of transfer layers. In contrast, both the PVD–TiN coating and plasma-nitrided layer exhibit excellent friction-reducing performance compared with the baseline Q&T surface, indicating that surface engineering is an effective approach for mitigating galling during aluminum hot stamping. At a moderate pressure of 4.5 MPa, the PVD–TiN surface produces a lower coefficient of friction than the nitrided surface. However, because the TiN coating is relatively thin, it can undergo local spallation under combined thermal effects and tangential shear. Once delamination occurs, the fresh metallic substrate is exposed, providing highly reactive sites that facilitate strong adhesion to the aluminum sheet. As a result, despite the lower measured friction coefficient, adhesive wear on the PVD–TiN die surface is more pronounced than on the nitrided die under this intermediate-pressure condition. By comparison, the plasma-nitrided layer contains nitride compound phases, such as Fe₃N and Fe₄N, which create a harder and more chemically stable near-surface region and can effectively suppress adhesion, thereby reducing material pickup and transfer. At a higher pressure of 5.4 MPa, the PVD–TiNTiN-modified die not only maintains a relatively low coefficient of friction but also benefits from TiN-related hard particles formed or retained at the interface. These particles can function as protective third-body constituents, reducing direct metal-to-metal contact and significantly alleviating adhesive wear. Under this high-pressure condition, the overall anti-galling performance of the PVD–TiN surface is superior to that of the nitrided surface. In contrast, the nitrided die under high pressure tends to experience plastic deformation, which generates agglomerated Fe–Cr alloy particles and worsens the interfacial contact state, ultimately destabilizing friction behavior and aggravating wear. In summary, PVD–TiN provides a more pronounced friction-reduction effect than plasma nitriding in the simulated 7075/H13 hot-stamping tribosystem and is particularly suitable for medium-to-low pressure hot-stamping applications where low friction is critical. Plasma nitriding, on the other hand, offers superior structural stability of the modified layer, making it better suited to heavy-load, high-pressure stamping scenarios in which resistance to deformation and long-term surface integrity are essential.