The new macrocyclic Schiff-base (2Z,7E,11E)-2,3-dichloro-8,11-dimethyl-1,4-dithia-7,12-diazacyclotetredeca-2,7,11-triene and its metal complexes with Cr(III), Mn(II), Fe(II), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) are reported. The reaction of tetrachloroethene with 2–mercaptoethylammonium chloride in mole ratios of 1:2 in the presence of methanolic potassium hydroxide gave the precursor (Z)-2,2`-(1,2-dichloroethene-1,2diyl)bis(sulfanediyl)diethanamine W. Condensation reaction of precursor with 2,5–hexanedione in mole ratios of 1:1 gave the new N2S2 macrocyclic Schiff-base L. Upon complex formation, the ligand behaves as a neutral tetradentate species forming monomeric complexes of general formulae [CrIII(L)Cl2]Cl, [MnII(L)Cl2], [NiII(L)(H2O)2]Cl2 and [MII(L )]Cl2 (M = Fe(II), Co(II), Cu(II), Zn(II) or Cd(II)). The mode of bonding and overall geometry of the complexes were determined through IR, UV-Vis, NMR, and mass spectral studies, magnetic moment measurements, elemental analysis, metal content, and conductance. These studies revealed octahedral geometries for the Cr(III), Mn(II) and Ni(II) complexes, square planar for Cu(II) complex and tetrahedral for the Fe(II), Co(II), Zn(II) and Cd(II) complexes.