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In the present work, firstly the novel monoxime (1) and asymmetric dioxime ligand (LH2) (2) derived 4′-hydroxyvalerophenone as ketone was prepared under optimum reaction conditions. Then, the bis-dioxime-based and boronic acid-capped groups containing Fe(II) and Co(II) complexes [(L)2M(X)2(BA)2] (3-6) (L= Dioxime, M = Fe(II) or Co(II), X= Cl2 or H2O and BA = Butyl boronic acid (BBA) or Ferrocene boronic acid (FBA)) were synthesized into a two-necked round-bottom flask by direct interaction of the dioxime ligand (2), and different boronic acid with metal salts (FeCl2.4H2O or CoCl2) without special requirement of any additional chemical process. The prepared ligands and their Fe(II) and Co(II) complexes were characterized by melting points, FT-IR, UV-Vis, LC-MS, NMR spectra (1 H and 13 C), elemental analysis, as well as magnetic susceptibility measurements. The spectroscopic results demonstrate that the proposed Fe(II) and Co(II) complexes consist of six-coordinated species and possess the octahedral geometry. The FT-IR spectra of the Fe(II) and Co(II) complexes reveal the existence of the characteristic peaks at range from 1208 to 1217 cm-1 corresponding to (B-O) stretching.