The aim of this dissertation was to develop new techniques for producing electrospun scaffolds for use in the tissue engineering of articular cartilage. We developed a novel method of imparting mechanical anisotropy to electrospun scaffolds that allowed the production of a single, cohesive scaffold with varying directions of anisotropy in different layers by employing insulating masks to control the electric field. We improved the quantification of fiber alignment, discovering that surface fibers in isotropic scaffolds show similar amounts of fiber alignment as some types of anisotropic scaffolds, and that cells align themselves in response to this subtle fiber alignment. We improved previous methods to improve cellular infiltration into tissue engineering scaffolds. Finally, we produced a new material with chondrogenic potential consisting of native unpurified cartilage which was electrospun as a composite with a synthetic polymer. This work provided advances in three major areas of tissue engineering:​ scaffold properties, cell-scaffold interaction, and novel materials.