Protein- and cell-based therapies represent highly promising strategies for regenerative medicine, immunotherapy, and oncology. However, these therapies are significantly limited by delivery considerations, particularly in terms of protein stability and dosing kinetics as well as cell survival, engraftment, and function. Hydrogels represent versatile and robust delivery vehicles for proteins and cells due to their high water content that retains protein biological activity, high cytocompatibility and minimal adverse host reactions, flexibility and tunability in terms of chemistry, structure, and polymerization format, ability to incorporate various biomolecules to convey biofunctionality, and opportunity for minimally invasive delivery as injectable carriers. This review highlights recent progress in the engineering of poly(ethylene glycol) hydrogels cross-linked using maleimide reactive groups for protein and cell delivery.