Each year, surgeons repair more than 300,000 injured tendon and ligament (T/L) tissues in the United States alone . Unfortunately, current treatments are limited, resulting in a clinical need for regenerated T/L tissues. Electrospun nanofibers are favorable for tissue engineering applications due to their resemblance in fiber diameter and morphology to extracellular matrix. We propose to utilize this biomimetic feature of nanofibers in the generation of scaffolds that also mimic the macrostructure of natural tissue. We hypothesize that scaffolds that recapitulate natural tissue structure over a range of dimensions will enhance natural tissue regeneration with progenitor cells. Here, we report on the fabrication and initial characterization of a novel biomimetic scaffold that begins to recapitulate the complex structure of a fascicle and endotenon of natural T/L. Electrospinning was employed to generate aligned nanofiber mats that were seeded with progenitor cells and subsequently assembled into a complex construct to represent a fascicle surrounded by the endotenon. The resulting scaffold physically resembled native T/L and demonstrated the ability to support progenitor cell attachment, viability, and proliferation. Currently, studies are underway to characterize the ability for these scaffolds to support and enhance progenitor cell differentiation toward the T/L lineage and demonstrate the use of these novel biomimetic scaffolds for T/L tissue engineering.