A new Schiff base Ligand (L)( where L= 3Z,3'Z)-3,3'-((2,2-dimethylpropane-1,3-diyl)bis(azanylyidene))bis(5chloroindolin-2-one) has been synthesized by condensation of 5-Chloroisatin and 2, 2-dimethyl propane-1, 3diamine respectively in the molar ratio of 2:1.The synthesized ligand(L) was used to synthesis metal complexes of transition metals ( Mn(II), Fe(II), Co(II), Ni(II), and Zn(II)). The ligand and its metal complexes have been characterized by elemental analysis, FT-IR, UV-Visible, ESI-Mass spectrometry and 1 H-NMR and 13 C-NMR spectra. On the basis of Spectral data it is revealed that the ligand is N, N, O, O tetradentate and coordinated to the metal ion to both azomethine N atoms and O atoms of lactum group. All the metal complexes show octahedral geometry except Ni(II) and Zn(II) they possess square planar geometry. The ligand and its metal complexes were tested for antibacterial activities. Metal Complexes showed better antibacterial activities as compare to Ligand.