We report infrared spectra of hydrogen-bonded phenol-amine clusters, phenol-NH₃, -N(CH₃)₃, -NH(C₂H₅)₂, and -N(C₂H₅)₃, prepared in jet expansions. The OH, NH, and CH stretching fundamentals were studied. Infrared-ultraviolet double-resonance techniques were utilized for vibrational spectroscopy of size-selected clusters. The OH stretch frequencies of the phenol moieties showed extremely large red-shifts from that of bare phenol, reflecting the strong proton affinities of the amines. Moreover, non-proton-transferred structures of the clusters were confirmed. The detailed structure of phenol-NH₃ was examined by ab initio calculations, which reproduced the observed infrared spectrum.