In mature individuals, hyaline cartilage demonstrates a poor intrinsic capacity for repair, thus even minor defects could result in progressive degeneration, impeding quality of life. Although numerous attempts have been made over the past years for the advancement of effective treatments, significant challenges still remain regarding the translation of in vitro cartilage engineering strategies from bench to bedside. This paper reviews the latest concepts on engineering cartilage tissue in view of biomaterial scaffolds, tissue biofabrication, mechanobiology, as well as preclinical studies in different animal models. The current work is not meant to provide a methodical review, rather a perspective of where the field is currently focusing and what are the requirements for bridging the gap between laboratory-based research and clinical applications, in light of the current state-of-the-art literature. While remarkable progress has been accomplished over the last 20 years, the current sophisticated strategies have reached their limit to further enhance healthcare outcomes. Considering a clinical aspect together with expertise in mechanobiology, biomaterial science and biofabrication methods, will aid to deal with the current challenges and will present a milestone for the furtherance of functional cartilage engineering.