A series of metal complexes have been synthesised using the Schiff base ligand, 4-hydroxypent-3-en-2- ylideneaminophenol, (L1) derived from the condensation reaction of 2-aminophenol with acetyl acetone in ethanol. This series of M-L1 complexes (M=Fe(III),Co(II),Mn(II), Cu(II) and Zn(II) ) were characterized by spectroscopic techniques (IR, UV-visible), elemental analysis, and conductivity measurement. The analytical results reveal that the Schiff base acted as a tridentate ligand and coordinated to the metal ion in a 1:1 M: L stoichiometric ratio. The Fe(III), Mn(II) and Co(II) complexes showed octahedral geometry, while the Zn(II) and Cu(II) complexes showed tetrahedral geometry. Invitro antibacterial activity of the Schiff base ligand and its metal complexes carried out on four bacterial strains (E. coli, P. aeruginosa, S. typhi, S. aureus) and four fungal strains (C. albicans ATCC 12C, C. albicans ATCC P37037, C. albicans ATCC P37039, C. neoformans) showed higher activity of the complexes compared to the ligand. The Schiff base and its metal complexes showed antioxidant (free radical scavenging) activities when compared to garlic acid.