Findings concerning the antiadhesive activity of cranberry phenolic compounds and their microbial-derived metabolites against Gram-negative ( Escherichia coli ATCC 53503 and DSM 10791) and Gram-positive ( Enterococcus faecalis 04-1) bacteria in T24 cells are reported. A-Type procyanidins (A2 and cinnamtannin B-1) exhibited antiadhesive activity (at concentrations ≥250 μM), a feature that was not observed for B-type procyanidins (B2). The metabolites hippuric acid and α-hydroxyhippuric acid also showed effective results at concentrations ≥250 μM. With regard to conjugated metabolites, sulfation seemed to increase the antiadhesive activity of cranberry-derived metabolites as 3-(3,4-dihydroxyphenyl)propionic acid 3- O-sulfate presented active results, unlike its corresponding nonsulfated form. In contrast, methylation decreased antiadhesive activity as 3,4-dihydroxyphenylacetic acid was found to be active but not its corresponding methylated form (4-hydroxy-3-methoxyphenylacetic acid). As a whole, this work sustains the antiadhesive activity of cranberry-derived metabolites as one of the mechanisms involved in the beneficial effects of cranberries against urinary tract infections.