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 nb initio calculations, which reproduced the observed infrared spectrum.