Regeneration of fibrocartilage at the tendon-bone insertion site in rotator cuff tears (RCTs) is challenging due to the complexity of its composition and mechanical properties. In this study, hierarchical, stretchable and stiff fibrous scaffolds composed of microfibers of poly (ε-caprolactone) (PCL) and nanofibers of chitosan (CS) were fabricated using stagger-electrospinning for augmentation of RCT-healing. It was found that the composite PCL-CS scaffolds had significantly improved strength and failure strain compared to the control CS scaffolds and increased stiffness compared to the control PCL scaffolds. These scaffolds also showed enhanced hydrophilicity, water absorption and faster degradation rate compared to the PCL scaffolds. They, additionally, demonstrated better fibroblast attachment and proliferation compared to the PCL scaffolds. Radiological and histological analysis revealed that the PCL-CS scaffolds enhanced new bone formation (mineralization), collagen and glycosaminoglycan expression (major components of extracellular matrix) compared with the PCL scaffolds. Furthermore, the torn tissues at the tendon-bone insertion site regenerated with the PCL-CS scaffolds showed higher strength and failure strain as well as stiffness compared to that with the PCL scaffolds. The above results have suggested that the hierarchical, stretchable and stiff fibrous scaffolds engineered using stagger-electrospinning boast great potential for augmentation of RCT-healing.