The rotator cuff and Achilles tendons along with the anterior cruciate ligament (ACL) are frequently injured with limited healing capacity. At the soft-hard tissue interface, enthesis is prone to get damaged and its regeneration in osteochondral defects is essential for complete healing. The current clinical techniques used in suturing procedures to reattach tendons to bones need much improvement for the generation of the native interface tissue, i.e., enthesis, for patients to regain their full functions. Recently, inspired by the composite native tissue, much effort has been made to fabricate composite scaffolds for enthesis tissue regeneration. The current review first focuses on the studies that used composite scaffolds for the regeneration of enthesis. Then, the use of polysaccharides for osteochondral tissue engineering is reviewed and their potential for enthesis regeneration is presented based on their supporting effects on osteo- and chondrogenesis. Gellan gum is selected and reviewed as a promising polysaccharide due to its unique osteogenic and chondrogenic activities that help avoid the inherent weakness of dissimilar materials in composite scaffolds. Additionally, original preliminary results showed that gellan gum supports collagen type I production and upregulation of osteogenic marker genes.