A series of Co(II), Ni(II), Cu(II), Zn(II) complexes have been synthesized with a benzothiazole azo dye containing tridentate (NNO) donor ligand 4-(((6-nitrobenzo[d]thiazol-2-yl)imino)methyl)benzene-1,3-diol derived from 2-amino-6-nitrobenzothiazole and 2,4-dihydroxybenzaldehyde. The structures of the novel ligand and metal complexes were identified and confirmed via various spectroscopic techniques (FT-IR,1H NMR,13C NMR, UV-Vis, mass spectrometry), TGA-DTA, powder X-ray diffraction, and DFT calculations. The optimal structural parameters and chemical reactivity of the ligand and metal complexes have been investigated using Density Functional Theory calculations (DFT/B3LYP,6-31G** and LanL2DZ basis sets) to provide insight about their frontier molecular orbitals (FMO) and molecular electrostatic potential (MESP). In vitro DPPH radical scavenging techniques have been used to assess the antioxidant activity of the ligand and complexes, indicating good antioxidant activity. The Ni(II) complex was the most potent with the lowest IC50 values. The in vitro antibacterial activities have been explored by screening against bacteria (Bacillus subtilis) and bacteria (E. coli) exhibiting significant activity against the tested strains of bacteria with Zn(II) complex as most potent with the lowest MIC value against E. coli and B. subtilis) and highest zone of inhibition against E. coli and B. subtilis at 1000 μg/mL concentration). The antifungal activity of complexes against Aspergillus niger and Candida albicans indicate that the Co(II) complex is most active for C. albicans and Zn(II) complex for A. niger .