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.