The condensation product of the reaction between aniline and salicylaldehyde was a 2-(2-hydroxybenzylidinemine)—aniline Schiff base bidentate ligand (L). L was used to generate complexes by interacting with the metal ions lanthanum(III), zirconium(IV), yttrium(III), and copper(II), in addition to cobalt(II). Various physicochemical techniques were utilized to analyze the synthesized L and its metal chelates, including elemental analysis (CHN), conductimetry (Λ), magnetic susceptibility investigations (μeff), Fourier-transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (1H NMR) spectroscopy, ultraviolet–visible (UV-Vis.) spectrophotometry, and thermal studies (TG/DTG). FT-IR revealed that the L molecule acted as a bidentate ligand by binding to metal ions via both the oxygen atom of the phenolic group in addition to the nitrogen atom of the azomethine group. Additionally, 1H NMR data indicated the formation of complexes via the oxygen atom of the phenolic group. An octahedral geometrical structure for all of the chelates was proposed according to the UV-Vis. spectra and magnetic moment investigations. Thermal analysis provided insight into the pattern of L in addition to its chelates’ breakdown. In addition, the investigation furnished details on the chelates’ potential chemical formulas, the characteristics of adsorbed or lattice H2O molecules, and the water that is coordinated but separated from the structure at temperatures exceeding 120 °C. The thermodynamic parameters utilizing Coats–Redfern in addition to Horowitz–Metzger equations were studied. The antimicrobial effectiveness of L and its chelates against distinct species of bacteria and fungi was studied using the disc diffusion method. Cu(II) and Y(III) chelates had significant antimicrobial activity against Staphylococcus aureus and Micrococcus luteus.