Chiral phenomena are ubiquitous in nature from macroscopic to microscopic, including the high chirality preference of small biomolecules, special steric conformations of biomacromolecules induced by it, as well as chirality-triggered biological and physiological processes. The introduction of chirality into the study of interface interactions between materials and biological systems leads to the generation of chiral biointerface materials, which provides a new platform for understanding the chiral phenomena in biological system, as well as the development of novel biomaterials and devices. This critical review gives a brief introduction to the recent advances in this field. We start from the fabrication of chiral biointerface materials, and further investigate the stereo-selective interaction between biological systems and chiral interface materials to find out key factors governing the performance of such materials in given conditions, then introduce some special functionalities and potential applications of chiral biointerface materials, and finally present our own thinking about the future development of this area (108 references).