Articular cartilage is the tissue at the junction of bones where it's highly organized anisotropic structure facilitates its biomechanical function during skeletal motion. The complex architecture and lack of a blood supply, however, limit the intrinsic ability of cartilage to regenerate following injury. The limitations in current approaches to focal cartilage repair demand innovative strategies to generate neocartilage. Throughout this dissertation research, I worked within the framework of the tissue engineering triad to: [1] characterize the chondrogenic differentiation capacity (chondrogenicity) of multiple cell types derived from adult human donors; [2] develop a scaffold-free system for large-scale tissue production; and [3] define the role of stimuli representative of the native joint environment, including low oxygen (physioxia) and dynamic mechanical compression, in driving the maturation of scaffold-free tissues.