Covalent drugs are becoming increasingly attractive in drug discovery, as they can enhance potency and selectivity for their molecular targets. Covalent inhibitors have been investigated for several therapeutic applications, including anti-cancer and anti-infection agents. However, there are only a few examples of covalent inhibitors targeting fungal pathogens. We have previously reported aromatic glycoconjugates (AGCs) capable of inhibiting the adhesion of Candida albicans to buccal epithelial cells. In this work, we synthesize novel derivatives of the AGCs to which we have added reactive functional groups, such as acryloyl and vinyl sulfones, and investigated their antifungal efficacy against Candida spp. Although the compounds were ineffective at clinically relevant concentrations, we found that some of the galactose derivatives featuring reactive groups were amongst the most active, so their ability to crosslink nucleophilic side chains was assessed in model reactions.