Cells are commonly surrounded by a nanodimensioned layer of glycoconjugates, called the “glycocalyx”. The question of how Glycocalyx Biochemistry functions in detail is of major interest in the realm of Biological Chemistry. In particular, comparisons of the Glycocalyx Biochemistry of cells that exhibit different states of health and disease may pave the way for hitherto unconsidered methods of treatment. The supramolecular (bio)chemistry of the glycocalyx goes beyond monovalent receptor-ligand interactions. Thus, unraveling the secrets of carbohydrate recognition on the cell surface opens the door to new concepts in Medicinal Chemistry. This video provides an overview of our work on the investigation of carbohydrate-specific bacterial adhesion. We utilize functional glycomimetics and specific glycoarrays that may be fabricated from photoswitchable glycosides.