Herein, we describe the synthesis and single crystal X-ray diffraction characterization of several Pb(II) complexes using Schiff base hydrazido-based ligands and different counterions (NO3−, I– and ClO4). In the three complexes reported in this work, the lead(II) metal exhibits a high coordination number (n > 8) and thus it is apparently not involved in tetrel bonding interactions. Moreover, the aromatic ligands participate in noncovalent interactions that play an important role in the formation of several supramolecular assemblies in the solid state of the three Pb(II) complexes. These assemblies have been analyzed by means of Hirshfeld surface analysis and DFT calculations.