Interfaces are a most important environment in natural and synthetic chemistries for a wide variety of processes, such as catalysis, recognition, separation, and so on. Naturally occurring systems have evolved to one handedness and the study of interfaces where biomolecules are located is a potentially revealing pursuit with regard to understanding the reasons and importance of stereochemistry in these environments. Equally, the spontaneous resolution of achiral and chiral compounds at interfaces could lead to explanations regarding the emergence of single handedness in proteins and sugars. Also, the attachment of biomolecules to surfaces leads to systems capable of stereoselective processes which may be useful for the applications mentioned above. The review covers systems ranging from small biomolecules studied under ultrapure conditions in vacuum to protein adsorption to surfaces in solution, and the techniques that can be used to study them.