We have demonstrated a practical and expedient diversity-oriented enzymatic strategy devised to generate a structurally diverse 150-member library of mono-and polyfluorinated Lewis x glycofluoroforms. The enzymes involved are shown to be highly tolerant for generating nucleotide-activated monofluorinated sugar donors, and for their glycosylation to fluorinated acceptors, with all possible 150 Lewis x glycofluoroforms being generated from six GlcNAc acceptors, five Gal, and five Fuc donors. Only natural forms of the enzymes have been used, the selection of which was considerably facilitated using a clickable imidazolium ITag for fast reaction monitoring.