In view of the global burden of wound care on healthcare systems, there is an urgent need for advanced therapeutic solutions to promote wound healing. Although conventional bilayer dressings contain layers with predefined mechanical properties, their mechanical architecture is static and may be vulnerable to disruption during 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 bilayer hydrogel stiffness was optimized to effectively replicate the distinct mechanical properties of the epidermis and dermis. This bilayer structure with cell-specific stiffness and distinct cell types promoted cell-specific proliferation and upregulated key wound-healing markers, including genes encoding collagen type I and α-smooth muscle actin. Furthermore, the hydrogel exhibited excellent shear-thinning and dynamic self-healing properties, ensuring high shape fidelity during extrusion-based three-dimensional 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.