In view of the global wound care burden on healthcare systems, there is an urgent need for advanced therapeutic solutions to promote wound healing. While conventional bilayer dressings statically define layer mechanics, they risk structural failure upon deformation. To address this limitation, we present a self-healing biomimetic bilayer hydrogel system that utilizes hyaluronic acid (HA) derivatives to emulate the mechanical and cellular heterogeneity of native skin tissue. The hydrogels were prepared by synthesizing carbodihydrazide-conjugated HA (HA-CDH) and crosslinking it with oxidized diol-modified HA in the presence of adipic acid dihydrazide. By adjusting the HA-CDH concentration, the stiffness of the bilayer hydrogel was optimized to effectively replicate the distinct mechanical properties of the epidermis and dermis. This bilayer structure with cell-specific stiffness and different cell types promoted cell-specific proliferation and upregulated key wound healing markers such as collagen type I and α-smooth muscle actin. Furthermore, the hydrogel exhibited excellent shear-thinning and dynamic self-healing properties that ensure high shape fidelity during extrusion-based 3D bioprinting of customized wound patches. In a full-thickness mouse wound model, these cell-laden bilayer patches promoted wound repair by significantly suppressing initial inflammatory responses, enhancing neovascularization, and facilitating balanced extracellular matrix remodeling without fibrotic thickening. The proposed self-healing bilayer hydrogel system stands as a promising, structurally dynamic solution for effective wound healing and has potential for further applications in tissue engineering.