Tissue Engineering is considered a promising route to address existing deficits of autografts and permanent synthetic prostheses for tendons and ligaments. However, the requirements placed on the scaffold material are manifold and include mechanical, biological and degradation-related aspects. In addition, scalable processes and FDA-approved materials should be applied to ensure the transfer into clinical practice. To accommodate these aspects, this work focuses on the high-scale fabrication of high-strength and highly oriented polycaprolactone (PCL) fibers with adjustable cross-sectional geometry and degradation kinetics applying melt spinning technology. Four different fiber cross-sections were investigated to account for potential functionalization and cell growth guidance. Mechanical properties and crystallinity were studied for a 24-week exposure to phosphate-buffered saline (PBS) at 37 °C. PCL fibers were further processed into scaffolds using multistage circular braiding with three different hierarchical structures. One structure was selected based on its morphology and scaled up in thickness to match the requirements for a human anterior cruciate ligament (ACL) replacement. Applying a broad range of draw ratios (up to DR9.25), high-strength PCL fibers with excellent tensile strength (up to 69 cN/tex) could be readily fabricated. The strength retention after 24 weeks in PBS at 37 °C was 83–93%. The following braiding procedure did not affect the scaffolds’ mechanical properties as long as the number of filaments and the braiding angle remained constant. Up-scaled PCL scaffolds resisted loads of up to 4353.88 ± 37.30 N, whilst matching the stiffness of the human ACL (111–396 N/mm). In conclusion, this work demonstrates the fabrication of highly oriented PCL fibers with excellent mechanical properties. The created fibers represent a promising building block that can be further processed into versatile textile implants for tissue engineering and regenerative medicine.