Injuries to tendons and ligaments are highly prevalent in the musculoskeletal system. Current treatments involve autologous transplants with limited availability and donor site morbidity. Tissue engineering offers a new approach through temporary load-bearing scaffolds. These scaffolds have to fulfill numerous requirements, the majority of which can be met using braiding combined with high-strength polycaprolactone (PCL) fibers. Considering regulatory requirements, several medical-grade PCL materials were assessed regarding their mechanical, degradational and cell biological properties. In the course of the investigation, an excellent fiber tensile strength of up to 850 MPa was achieved. The fibers were braided into multilayer scaffolds and scaled to match the human ACL. These were characterized regarding their morphology and their mechanical and degradational properties. Two strategies were followed to provide biological cues: (a) applying a chitosan-graft-PCL surface modification and (b) using non-circular fiber morphologies as topographical stimuli. Cell vitality assays showed generally positive cytocompatibility and no impairments due to the surface modification or material grade. The best cell vitality was achieved with a scaffold consisting of snowflake-shaped monofilaments combined with a 25° braiding angle. The surface modification equips the scaffold with a release platform for function molecules (as recently demonstrated) so that a holistic approach to addressing the numerous requirements is provided.