Virulence and the extent to which a microbe will cause disease are determined by dynamic host-pathogen interactions. It is now recognized that many of the processes involved depend upon a complement of carbohydrate structures associated with both the host and the invading microorganism, collectively termed the host-pathogen glycome. As glycomics tools and technologies develop, we are gaining a broader appreciation for the exquisite diversity of bacterial glycans and their role in pathogenesis and host immunity. Though deciphering the interactions between the host and the bacterial glycome is challenging and understudied, it promises to unveil avenues for novel biomedical applications in the fields of diagnostics, therapeutics, and vaccines that will reduce the burden of infectious diseases. This review will focus on the impact of bacterial glycoconjugates in host-pathogen interactions using specific examples and highlight the biomedical applications that stem from advances in our understanding.