Skin is a complex tissue and acts as a barrier against biological, chemical, and physical agents. Rupture of this tissue due to damage leads to disruption of the mucosal lining and results in its failure. Bioactive glass (BG) has emerged in past years as a promising material to assist wound healing. Although BG has been used mainly in bone tissue engineering, its application in soft tissue has been widely investigated. BG can promote fibroblast proliferation and migration, which is important for wound repair. BG can also be obtained by the incorporation of therapeutic ions and phytopharmaceuticals into its structure. Among these materials, cobalt (Co) and curcumin (Cur) deserve to be highlighted. Co is well known for its ability to activate hypoxia, which improves angiogenesis and assists in the formation of blood vessels. On the other hand, Cur is a phytopharmaceutical with anti-infectious, anti-inflammatory, and wound-healing properties. In this work, submicron-sized BG particles loaded with Co and Cur were used in a dressing system based on polyvinyl alcohol (PVA)/chitosan (CH) foams. PVA is one of the most used synthetic polymers in drug delivery systems and wound management. CH is a widely used biomaterial due to its capacity to promote cell differentiation and tissue growth. In this study, different amounts of Co (up to 5 mol%) were initially incorporated into BG by a sol-gel approach. These materials were then soaked in a Cur-containing solution to load this compound into the pore structure of BG. The as-obtained samples were subsequently inserted into PVA/CH foams, giving rise to composite dressings. As far as we know, this is the first time that this approach is reported, which reinforces the novelty of this study. The obtained materials were examined according to their structural and biological properties. We expect that the composite dressings prepared could accelerate the wound healing process and stimulate angiogenic and anti-inflammatory properties.