Approximately 2 million Achilles tendon sports-related injuries are diagnosed yearly of which over 250,000 require surgical intervention. During the healing process, after this surgical repair, the formation of scar tissue will dominate over well-aligned collagen fibers found at the native attachment. This scar tissue is weaker than the native tissue and is not well integrated into the bone, which makes them more prone to failure. Therefore, this research aimed at developing a biodegradable gradient scaffold to support enthesis regeneration. To this end, natural and synthetic polymers were synthesized and combined into a hybrid scaffold: acrylate- or norbornene-endcapped urethane-based polymers (AUP and NUP) and thiolated gelatin (GEL-SH). After physico-chemical characterization, the AUP and NUP polymers were optimized for 3D extrusion printing and 3D indirect printing using PVA molds. The fabricated scaffolds were characterized physico-chemically and through in vitro biological testing. The biological assays indicated biocompatibility and both early and late markers for osteogenic differentiation. Further work will include the differentiation of the MSCs into the different cell types present in the enthesis zones.