The chiralities of chiral drugs have been investigated extensively with the purpose of enlightening the role of chirality in drug action. Proteomics, though in its infancy, has recently emerged as the foremost technology in drug development research, possessing the advantage of providing more useful information about an organism than genomics, as it directly addresses the level of genome products and their interactions. In this review, we will discuss the background of chiral drug investigation from which contemporary drug chirality research has emerged, the techniques involved in proteomics technology, the application of proteomics in this exciting area, and the perspectives in future applications of this field.