Drug discovery and development has been garnering an increasing trend of research due to the growing incidence of the diverse types of diseases. Recently, drug repositioning, also known as drug repurposing, has been emerging parallel to cancer and tissue engineering studies. Drug repositioning involves the application of currently approved or even abandoned drugs as alternative treatments to other diseases or as biomaterials in other fields including cell therapy and tissue engineering. In this review, the advancement of the antiangiogenesis drugs that were used as treatment for cancer and other diseases, with particular focus on bevacizumab, will be described. This will include an overview of the nature and progression of osteoarthritis (OA), one of the leading global degenerative diseases that cause morbidity, and the development of its therapeutic strategies. In addition, this will also feature the nonsteroidal anti-inflammatory drugs that are commonly prescribed for OA and the benefits of repositioning bevacizumab as alternative treatments for other diseases and as biomaterials for cartilage regeneration. To date, a few number of studies, employing different modes of administration and varying dosages in diverse animal models, have shown that bevacizumab can be used as a signal and can promote both in vitro and in vivo cartilage regeneration. However, other antiangiogenesis drugs and their effects in chondrogenesis and cartilage regeneration are also worth investigating.